Issue 34, 2017

Total syntheses of smenothiazoles A and B

Abstract

Concise total syntheses of smenothiazoles A (1) and B (2), two distinguished vinyl chloride containing natural products isolated from the marine sponge S. aurea, have been developed. Silastannation, Stille reaction and a carefully controlled desilylchlorination were employed as key steps to construct unique polyketide acid fragments, and the optimized reaction conditions avoided migration of 2,5-diene to a 2,4-conjugated system. This report unambiguously confirmed the structures of both natural products.

Graphical abstract: Total syntheses of smenothiazoles A and B

Supplementary files

Article information

Article type
Paper
Submitted
23 Jul 2017
Accepted
09 Aug 2017
First published
09 Aug 2017

Org. Biomol. Chem., 2017,15, 7196-7203

Total syntheses of smenothiazoles A and B

X. Ma, Y. Chen, S. Chen, Z. Xu and T. Ye, Org. Biomol. Chem., 2017, 15, 7196 DOI: 10.1039/C7OB01818E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements