Enantioselective Total Syntheses of Acylfulvene, Irofulven, and the Agelastatins 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 Enantioselective Total Syntheses of Acylfulvene, Irofulven, and the Agelastatins PDF full book. Access full book title Enantioselective Total Syntheses of Acylfulvene, Irofulven, and the Agelastatins by Dustin Scott Siegel. Download full books in PDF and EPUB format.
Author: Dustin Scott Siegel
Publisher:
ISBN:
Category :
Languages : en
Pages : 285
Get Book Here
Book Description
I. Enantioselective Total Synthesis of ( - )-Acylfulvene, and ( - )-Irofulven We report the enantioselective total synthesis of ( - )-acylfulvene and ( - )-irofulven, which features metathesis reactions for the rapid assembly of the molecular framework of these anti tumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketene thioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent, IPNBSH, for a late stage reductive allylic transposition reaction, and (4) the final ring-closing metathesis/dehydrogenation sequence for the formation of ( - )-acylfulvene and ( - )-irofulven. II. Total Synthesis of the ( - )-Agelastatin Alkaloids The pyrrole-imidazole super-family of marine alkaloids, derived from linear clathrodinlike precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that have a tetracyclic molecular framework incorporating C4-C8 and C7-N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of the agelastatin alkaloids, including the first total syntheses of agelastatins C and E. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones.
Author: Dustin Scott Siegel
Publisher:
ISBN:
Category :
Languages : en
Pages : 285
Get Book Here
Book Description
I. Enantioselective Total Synthesis of ( - )-Acylfulvene, and ( - )-Irofulven We report the enantioselective total synthesis of ( - )-acylfulvene and ( - )-irofulven, which features metathesis reactions for the rapid assembly of the molecular framework of these anti tumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketene thioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent, IPNBSH, for a late stage reductive allylic transposition reaction, and (4) the final ring-closing metathesis/dehydrogenation sequence for the formation of ( - )-acylfulvene and ( - )-irofulven. II. Total Synthesis of the ( - )-Agelastatin Alkaloids The pyrrole-imidazole super-family of marine alkaloids, derived from linear clathrodinlike precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that have a tetracyclic molecular framework incorporating C4-C8 and C7-N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of the agelastatin alkaloids, including the first total syntheses of agelastatins C and E. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones.
Author: Baldev Kumar
Publisher: Alpha Science Int'l Ltd.
ISBN: 9781842652824
Category : Science
Languages : en
Pages : 318
Get Book Here
Book Description
"Starting with photosynthesis, the authors present a very lucid and logical approach from CO[subscript 2] and H[subscript 2]O to complicated structures of alkaloids, terpenes and many other natural products based on the basic principles of Organic reaction mechanism which though taken from other research studies, have been shown to be followed in nature. In addition to the basic formulations of Acetate hypothesis, and Mevlonic pathways, newer non-mevalonic paths have also been discussed and differences pointed out. This book discusses natural products in which basic principles are involved e.g. in alkaloids biosynthesis and basic amino acids which show their pathway in biosynthesis." "The material has been arranged in a sequence as to how a teacher of biosynthesis should/would teach this subject."--BOOK JACKET.
