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Total Synthesis and Biological Evaluation of Apratoxin E and Its C30 Epimer: Configurational Reassignment of the Natural Product.

ABSTRACT: Apratoxin E provided the inspiration for the design of apratoxin A/E hybrids under preclinical development. Through total synthesis using two different strategies, it was determined that the originally proposed configuration of the thiazoline at C30 is opposite from that in apratoxin A, in contrast to previous assumptions on biosynthetic grounds. The epimer and true natural apratoxin E were synthesized, and the biological activities were evaluated.

SUBMITTER: Wu P

PROVIDER: S-EPMC5386831 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Total Synthesis and Biological Evaluation of Apratoxin E and Its C30 Epimer: Configurational Reassignment of the Natural Product.

Wu Ping P Cai Weijing W Chen Qi-Yin QY Xu Senhan S Yin Ruwen R Li Yingxia Y Zhang Wei W Luesch Hendrik H

Organic letters 20161010 20

Apratoxin E provided the inspiration for the design of apratoxin A/E hybrids under preclinical development. Through total synthesis using two different strategies, it was determined that the originally proposed configuration of the thiazoline at C30 is opposite from that in apratoxin A, in contrast to previous assumptions on biosynthetic grounds. The epimer and true natural apratoxin E were synthesized, and the biological activities were evaluated. ...[more]

PMID: 27723359

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