Progress Towards the Total Synthesis of Amphidinolide E PDF Download
Are you looking for read ebook online? Search for your book and save it on your Kindle device, PC, phones or tablets. Download Progress Towards the Total Synthesis of Amphidinolide E PDF full book. Access full book title Progress Towards the Total Synthesis of Amphidinolide E by Andrew Frederick Nolting. Download full books in PDF and EPUB format.
Author: Andrew Frederick Nolting
Publisher:
ISBN:
Category :
Languages : en
Pages : 194
Get Book Here
Book Description
Author: Andrew Frederick Nolting
Publisher:
ISBN:
Category :
Languages : en
Pages : 194
Get Book Here
Book Description
Author: William E. Brenzovich (Jr.)
Publisher:
ISBN:
Category : Antineoplastic agents
Languages : en
Pages : 916
Get Book Here
Book Description
Author: Jesse D. Carrick
Publisher:
ISBN:
Category :
Languages : en
Pages : 170
Get Book Here
Book Description
Author: Nicholas A. Morra
Publisher:
ISBN:
Category :
Languages : en
Pages :
Get Book Here
Book Description
A second generation catalyst for the Mukaiyama oxidative cyclization for the formation of trans-THF rings is described. Co(nmp)2, displays increased stability to the reaction conditions, resulting in lower catalyst loadings, lower reaction temperatures, and significantly higher purity and yields of the products. Three procedures have been developed with this new water-soluble catalyst that greatly simplifies the post-reaction purification, making this procedure the premier method of forming trans-THF rings. This new catalyst has been applied towards the total synthesis of the potently bioactive macrocycle, Amphidinolide C. Herein we report the successful synthesis of several fragments of the natural product, and our attempts at coupling them to complete the synthesis. The C(1)-C(9) was achieved via two routes, both utilizing the highly effective oxidation catalyst Co(nmp)2 to form the methyl substituted trans-THF ring. Synthetic highlights include a regioselective Shi epoxidation, and the design and introduction of a novel Lewis acid (BF2OBn×OEt2) to facilitate a stereoselective reductive epoxide opening. The C(18)-C(34) fragment was also achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. Synthetic highlights of this fragment include a selective methylation of a diyne, and a highly selective alkynylation of a THF aldehyde, achieving excellent dr (>20:1) without the addition of an external chiral compound. Advanced intermediates comprising the entirety of the carbon backbone of the molecule have been synthesized, which in theory could complete the total synthesis in as few as two bond forming steps.
Author: Porino J. Va
Publisher:
ISBN:
Category : Macrolide antibiotics
Languages : en
Pages : 472
Get Book Here
Book Description
Detailed in the following thesis are stereocontrolled syntheses of four amphidinolide E stereoisomers: amphidinolide E, 2- epi -amphidinolide E, 19- epi -amphidinolide E, and 2- epi -19- epi -amphidinolide E. Preliminary studies targeting amphidinolide E led to the inadvertent syntheses of 2- epi -amphidinolide E and 2- epi -19- epi -amphidinolide E due to an unexpected and highly selective C2 inversion during the modified Yamaguchi esterification step involving the (2 S, 3 S) (CO) 3 Fe-complexed dienoic acid. Ultimately, this C2 inversion phenomenon was discovered and use of the (2 S, 3 R) (CO) 3 Fe-complexed dienoic acid enabled the syntheses of amphidinolide E and 19- epi -amphidinolide E. Featured in the synthetic route is the synthesis of the tetrahydrofuran core of amphidinolide E through a highly diastereoselective [3+2] annulation reaction. Also noteworthy, are the synthesis of the 19-membered macrocycle via a ring closing metathesis reaction and use of the (CO) 3 Fe-unit as a diene protecting group to enable an efficient esterification of the hindered alcohol substrate.
Author: Christopher Michael Verdon
Publisher:
ISBN:
Category : Drugs
Languages : en
Pages : 374
Get Book Here
Book Description
Author: Daniel A. Mills
Publisher:
ISBN:
Category :
Languages : en
Pages :
Get Book Here
Book Description
Author: Brian J. Myers
Publisher:
ISBN:
Category :
Languages : en
Pages : 428
Get Book Here
Book Description
Author: Natalie E. Campbell
Publisher:
ISBN:
Category :
Languages : en
Pages :
Get Book Here
Book Description
Author: Steven Edward Hall
Publisher:
ISBN:
Category : Diels-Alder reaction
Languages : en
Pages : 344
Get Book Here
Book Description
