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Author: Drew James Adams
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 502
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Author: Drew James Adams
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 502
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Author: Meiliana Tjandra
Publisher:
ISBN:
Category :
Languages : en
Pages : 299
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Book Description
I. Total Synthesis of All Class III Galbulimima Alkaloids We describe the total synthesis of (+)- and (-)-galbulimima alkaloid 13, (-)-himgaline anad (-)-himbadine. The absolute stereochemistry of natural (-)-galbulimima alkaloid 13 is revised to 2S. Sequential use of catalytic cross-coupling and cross-metathesis reactions followed by an intramolecular Diels-Alder reaction provided the required trans-decalin AB-ring system and masked the Cl 6-carbonyl as an N-vinyl carbamate for late stage unveiling in the form of the necessary C16-enone. A vinyl-radical cyclization secured the C-ring while successful execution of our strategy for introduction of the CDE-ring system in complex galbulimima alkaloids provided the target pentacycle with complete diastereoselection. II. Total Synthesis of (-)-Himandrine We describe the first total synthesis of (-)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels- Alder reaction in the rapid synthesis of the tricycle ABC-ring system in enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of our biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the F-ring in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate.
Author: Unmesh Shah
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 532
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Author: Diana Katharine Hunt
Publisher:
ISBN:
Category :
Languages : en
Pages : 413
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Book Description
I. Total Synthesis of Galbulimima Alkaloids. The total synthesis of enantiomerically enriched (+)- and (-)-galbulimima alkaloid 13 is outlined. Sequential use of catalytic cross-coupling and cross-metathesis reactions followed by an intramolecular Diels-Alder reaction provided the required trans-decalin AB ring system and masked the C16-carbonyl as an N-vinyl carbamate for late stage oxidative unveiling as the corresponding C16-enone. Completely diastereoselective introduction of the C-ring via radical cyclization chemistry followed by an enamine-ketone addition for construction of the CDE-ring system allowed rapid entry to the pentacyclic core of these alkaloids. The absolute stereochemistry of natural (-)-galbulimima alkaloid 13 is now unambiguously revised to 2S.
Author: Kimberly Katherine Larson
Publisher:
ISBN:
Category :
Languages : en
Pages : 304
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This dissertation describes our strategy for the total synthesis of Galbulimima alkaloid ()-G.B. 13. First, an overview of the isolation and structural classification of the twenty-eight alkaloids in the Galbulimima family is presented. Proposals for the biosyntheses of these natural products as well as the determination of their absolute stereochemical relationships are discussed. Additionally, the biological and medicinal properties of himbacine, another Galbulimima alkaloid, are presented. The four total syntheses of alkaloid G.B. 13 that have been completed by research groups other than our own are briefly examined. Our own total synthesis of ()-G.B. 13 was accomplished in eighteen linear steps from commercially available starting materials. A detailed account of our synthetic endeavors, which include the rational development of both an allylic alcohol transposition under modified Parikh-Doering conditions and an unprecedented rhodium(I)-catalyzed addition of an aryl boronic ester into an unactivated ketone carbonyl, is described. The completion of this synthesis demonstrates the synthetic utility of a pyridine moiety as a piperidine surrogate. The last section of this dissertation conveys our work developing a novel palladium(0)-mediated transformation that provides stereochemically-defined enals, enones, and dienones through the union of aryl and vinyl halides with divinyl and enyne carbinol coupling partners. This reaction is believed to proceed through a cyclopropanol intermediate and to involve a novel skeletal reorganization. Experimental observations in support of our proposed mechanism, as well as a complete substrate scope, are presented.
Author: John Arthur Halleday
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 232
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Author:
Publisher: Academic Press
ISBN: 012812198X
Category : Science
Languages : en
Pages : 388
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Book Description
The Alkaloids, Volume 78 is the latest update in a series that has not only covered the topic for more than 60 years, but is also touted as the leading book series in the field of alkaloid chemistry. Topics of note in this updated volume include The Acridone Alkaloids, The Galbulimima-Alkaloids, the Total Synthesis of Lundurine and Related Alkaloids: Recent Applications, The Moschamine-Related Indole Alkaloids, and Alkaloids of the Lauraceae. In more than 75 volumes, all aspects of alkaloids, including chemistry, biology and pharmacology are covered in high-quality, timeless reviews written by renowned experts in the field. - Contains the latest information on the study of alkaloids - Covers their chemistry, biology, pharmacology and medical applications - Presents more than 75 volumes in this interesting field of study
Author: Matthew M.W. McLachlan
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 356
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Author: Tanweer A. Khan
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Author: Hans-Joachim Knoelker
Publisher: Springer Science & Business Media
ISBN: 3642255280
Category : Science
Languages : en
Pages : 268
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Book Description
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-
