Author: Kyle William Rugg
Publisher:
ISBN:
Category :
Languages : en
Pages : 307
Book Description
"Part I. The Second-Generation Total Synthesis of (-)-Nakadomarin A The second-generation total synthesis of (-)-nakadomarin A (1) has been described. A robust sequence toward the bicyclic lactam has been developed, allowing its production on > 5 g scale. This has been enabled by a number of significant improvements, including increased diastereoselectivity for the key SN2' cyclobutane formation, a scalable cyclobutanecarboximine formation/retro-aza-Claisen sequence, and the removal of a step from the longest-linear sequence by use of isocyanate addition to the bicyclic lactam in lieu of a two-step protocol. The Michael addition/spirocyclization's catalytic potential has been investigated, and a robust and scalable method for the synthesis of the spirocycle has been deployed. After pentacycle formation, macrocyclization, and reduction, (-)-nakadomarin A (1) is afforded with production of the target on over 0.5 g scale. This has resulted in a total synthesis of 1 in 16 steps (longest linear) and 6.5% overall yield. Part II. Studies Toward the Total Synthesis of (-)-Apoptolidin A A route toward the potent and selective apoptosis inducer (-)-apoptolidin A has been outlined. Production of the lactone comprising the southwestern quadrant of the natural product on scale by a previously described route has been investigated. Small-scale success in generating the lactone was ineffective on larger scales using the existing protocol due to the sensitive nature of an intermediate Diels-Alder adduct. Important advancement in material throughput was achieved by implementation of a robust two-step protocol for generating a critical intermediate alcohol on larger scales. Combined with the improvement of a deallylation protocol, a scalable route to the lactone of the southwestern quadrant of (-)-apoptolidin A has been established. With this, the completion of the southern hemisphere and aglycone of (-)-apoptolidin A will be accessible"--Pages x-xi.
I. Second Generation Total Synthesis of (-)-Nakadomarin A
Author: Kyle William Rugg
Publisher:
ISBN:
Category :
Languages : en
Pages : 307
Book Description
"Part I. The Second-Generation Total Synthesis of (-)-Nakadomarin A The second-generation total synthesis of (-)-nakadomarin A (1) has been described. A robust sequence toward the bicyclic lactam has been developed, allowing its production on > 5 g scale. This has been enabled by a number of significant improvements, including increased diastereoselectivity for the key SN2' cyclobutane formation, a scalable cyclobutanecarboximine formation/retro-aza-Claisen sequence, and the removal of a step from the longest-linear sequence by use of isocyanate addition to the bicyclic lactam in lieu of a two-step protocol. The Michael addition/spirocyclization's catalytic potential has been investigated, and a robust and scalable method for the synthesis of the spirocycle has been deployed. After pentacycle formation, macrocyclization, and reduction, (-)-nakadomarin A (1) is afforded with production of the target on over 0.5 g scale. This has resulted in a total synthesis of 1 in 16 steps (longest linear) and 6.5% overall yield. Part II. Studies Toward the Total Synthesis of (-)-Apoptolidin A A route toward the potent and selective apoptosis inducer (-)-apoptolidin A has been outlined. Production of the lactone comprising the southwestern quadrant of the natural product on scale by a previously described route has been investigated. Small-scale success in generating the lactone was ineffective on larger scales using the existing protocol due to the sensitive nature of an intermediate Diels-Alder adduct. Important advancement in material throughput was achieved by implementation of a robust two-step protocol for generating a critical intermediate alcohol on larger scales. Combined with the improvement of a deallylation protocol, a scalable route to the lactone of the southwestern quadrant of (-)-apoptolidin A has been established. With this, the completion of the southern hemisphere and aglycone of (-)-apoptolidin A will be accessible"--Pages x-xi.
Publisher:
ISBN:
Category :
Languages : en
Pages : 307
Book Description
"Part I. The Second-Generation Total Synthesis of (-)-Nakadomarin A The second-generation total synthesis of (-)-nakadomarin A (1) has been described. A robust sequence toward the bicyclic lactam has been developed, allowing its production on > 5 g scale. This has been enabled by a number of significant improvements, including increased diastereoselectivity for the key SN2' cyclobutane formation, a scalable cyclobutanecarboximine formation/retro-aza-Claisen sequence, and the removal of a step from the longest-linear sequence by use of isocyanate addition to the bicyclic lactam in lieu of a two-step protocol. The Michael addition/spirocyclization's catalytic potential has been investigated, and a robust and scalable method for the synthesis of the spirocycle has been deployed. After pentacycle formation, macrocyclization, and reduction, (-)-nakadomarin A (1) is afforded with production of the target on over 0.5 g scale. This has resulted in a total synthesis of 1 in 16 steps (longest linear) and 6.5% overall yield. Part II. Studies Toward the Total Synthesis of (-)-Apoptolidin A A route toward the potent and selective apoptosis inducer (-)-apoptolidin A has been outlined. Production of the lactone comprising the southwestern quadrant of the natural product on scale by a previously described route has been investigated. Small-scale success in generating the lactone was ineffective on larger scales using the existing protocol due to the sensitive nature of an intermediate Diels-Alder adduct. Important advancement in material throughput was achieved by implementation of a robust two-step protocol for generating a critical intermediate alcohol on larger scales. Combined with the improvement of a deallylation protocol, a scalable route to the lactone of the southwestern quadrant of (-)-apoptolidin A has been established. With this, the completion of the southern hemisphere and aglycone of (-)-apoptolidin A will be accessible"--Pages x-xi.
Studies Towards the Total Synthesis of Nakadomarin A.
Author: Thomas Haimowitz
Publisher:
ISBN: 9781109985320
Category :
Languages : en
Pages : 360
Book Description
*Please refer to dissertation for diagram.
Publisher:
ISBN: 9781109985320
Category :
Languages : en
Pages : 360
Book Description
*Please refer to dissertation for diagram.
Marine Natural Products
Author: Hiromasa Kiyota
Publisher: Springer Nature
ISBN: 9811646376
Category : Science
Languages : en
Pages : 510
Book Description
This book is a compilation of the latest achievements of leading researchers in marine natural products with extremely diverse structures and biological activities. It presents discussions of isolation, structure elucidation, biosynthesis, total synthesis, and biochemical properties of the compounds with characteristic structures such as macrolides, cyclic depsipeptides, alkaloids, and water-soluble heterocyclic low-molecular-weight compounds, from sponges, bacteria, cyanobacteria, flagellates, and other such organisms. The book especially focuses on heterocyclic natural products as a title in the book series, Topics in Heterocyclic Chemistry.
Publisher: Springer Nature
ISBN: 9811646376
Category : Science
Languages : en
Pages : 510
Book Description
This book is a compilation of the latest achievements of leading researchers in marine natural products with extremely diverse structures and biological activities. It presents discussions of isolation, structure elucidation, biosynthesis, total synthesis, and biochemical properties of the compounds with characteristic structures such as macrolides, cyclic depsipeptides, alkaloids, and water-soluble heterocyclic low-molecular-weight compounds, from sponges, bacteria, cyanobacteria, flagellates, and other such organisms. The book especially focuses on heterocyclic natural products as a title in the book series, Topics in Heterocyclic Chemistry.
Total Synthesis of (-)-Nakadomarin A.
Author: Bichu Cheng
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
A convergent and scalable total synthesis of polycyclic manzamine alkaloid (-)-nakadomarin A is described. Unsaturated bicyclic lactam fragment A was prepared from acrolein in 5 steps, and macrolactam fragment B was prepared from 3-furfural in 7 steps. A double Michael addition reaction (or cyclization) between A and B provided the desired fragment coupling product C in 79% yield and 9:1 dr on more than one-gram scale. Completion of the total synthesis of (-)-nakadomarin A was then achieved in a one-pot transformation from compound C.
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
A convergent and scalable total synthesis of polycyclic manzamine alkaloid (-)-nakadomarin A is described. Unsaturated bicyclic lactam fragment A was prepared from acrolein in 5 steps, and macrolactam fragment B was prepared from 3-furfural in 7 steps. A double Michael addition reaction (or cyclization) between A and B provided the desired fragment coupling product C in 79% yield and 9:1 dr on more than one-gram scale. Completion of the total synthesis of (-)-nakadomarin A was then achieved in a one-pot transformation from compound C.
Towards the Total Synthesis of Nakadomarin A
Author: Chao Xu
Publisher:
ISBN:
Category : Marine natural products
Languages : en
Pages : 222
Book Description
Publisher:
ISBN:
Category : Marine natural products
Languages : en
Pages : 222
Book Description
Studies Towards the Total Synthesis of Nakadomarin A.
Author: Emilie Laloy Poltronieri
Publisher:
ISBN:
Category : Marine natural products
Languages : en
Pages : 205
Book Description
Publisher:
ISBN:
Category : Marine natural products
Languages : en
Pages : 205
Book Description
Cascade Strategies for Chemical Synthesis
Author: Carolyn Gauntlett
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Total Synthesis of (-)-nakadomarin A and an Approach to the Diazatricyclic Core of the Madangamines
Author: Andrew F. Kyle
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Studies Towards the Total Synthesis of (-)-Nakadomarin A
Author: Hui Wang
Publisher:
ISBN:
Category :
Languages : en
Pages : 562
Book Description
"The total synthesis of Nakadomarin A has been described. The intramolecular syn-SN2' cyclization to form the retro-aza-Claisen precursor cyclobutane was optimized. An efficient asymmetric synthesis of a key bicyclic lactam precursor was completed based on previous research efforts. A series of model studies were completed in order to help understand the behavior of a putative 3-aza-6-?-electrocyclic ring closure, a key step in our synthetic strategy. The construction of the spirohexacycle ring system was investigated and optimized. The pentacyclic ring system was formed via a selective lactam reduction followed by Friedel-Craft ring closure. Alkyne metathesis catalyzed by Mo-catalyst afforded the 15-membered ring. Desulfonation of bulky triisopropylbenzenesulfonyl function group was achieved."--Page vi.
Publisher:
ISBN:
Category :
Languages : en
Pages : 562
Book Description
"The total synthesis of Nakadomarin A has been described. The intramolecular syn-SN2' cyclization to form the retro-aza-Claisen precursor cyclobutane was optimized. An efficient asymmetric synthesis of a key bicyclic lactam precursor was completed based on previous research efforts. A series of model studies were completed in order to help understand the behavior of a putative 3-aza-6-?-electrocyclic ring closure, a key step in our synthetic strategy. The construction of the spirohexacycle ring system was investigated and optimized. The pentacyclic ring system was formed via a selective lactam reduction followed by Friedel-Craft ring closure. Alkyne metathesis catalyzed by Mo-catalyst afforded the 15-membered ring. Desulfonation of bulky triisopropylbenzenesulfonyl function group was achieved."--Page vi.
The Alkaloids
Author:
Publisher: Academic Press
ISBN: 0128209844
Category : Science
Languages : en
Pages : 370
Book Description
The Alkaloids, Volume 84, is the newest release in a series that has covered the topic for more than 60 years. As the esteemed, leading reference in the field of alkaloid chemistry, this series covers all aspects of alkaloids, including their chemistry, biology and pharmacology. Sections are presented as high-quality, timeless reviews written by renowned experts in the field. - Provides the latest information on the study of alkaloids - Covers their chemistry, biology, pharmacology and medical applications - Contains more than 70 published volumes in this interesting field of study
Publisher: Academic Press
ISBN: 0128209844
Category : Science
Languages : en
Pages : 370
Book Description
The Alkaloids, Volume 84, is the newest release in a series that has covered the topic for more than 60 years. As the esteemed, leading reference in the field of alkaloid chemistry, this series covers all aspects of alkaloids, including their chemistry, biology and pharmacology. Sections are presented as high-quality, timeless reviews written by renowned experts in the field. - Provides the latest information on the study of alkaloids - Covers their chemistry, biology, pharmacology and medical applications - Contains more than 70 published volumes in this interesting field of study