Issue 9, 2016

Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

Abstract

An asymmetric synthesis of the C1 to C11 and C14 to C18 fragments of the macrocyclic portion of the antibiotic Leucascandrolide A was achieved in 21 total steps from an achiral dienoate. The key 4-hydroxy-2,5-pyran portion of the natural product was established by oxy-Michael cyclization of a 5,7,9,11-tetraol intermediate, which in turn was established by an iterative asymmetric-hydration of dienoates. Alternative strategies for establishing the polyol stereochemistry were explored.

Graphical abstract: Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

Supplementary files

Article information

Article type
Research Article
Submitted
20 jun 2016
Accepted
12 jul 2016
First published
12 jul 2016

Org. Chem. Front., 2016,3, 1120-1125

Author version available

Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

T. J. Hunter, J. Zheng and G. A. O'Doherty, Org. Chem. Front., 2016, 3, 1120 DOI: 10.1039/C6QO00284F

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