Issue 29, 2017

Strategy towards the enantioselective synthesis of schiglautone A

Abstract

Herein is described a convergent enantioselective route to an advanced intermediate in the synthesis of schiglautone A, a Schisandra triterpenoid with an unusual architecture. The synthetic route to this intermediate displaying 6 of the 7 stereocenters builds upon two fragments, an aldehyde elaborated from the Wieland–Miescher ketone, and a ketone. The preparation of the latter features a lithiation–borylation enzymatic resolution sequence, which led to the formation of the desired product with high enantio- and diastereoselectivities. After aldol coupling of the two fragments, the final quaternary stereocenter was installed by cyclopropane opening. The functionalized intermediate was isolated as a single diastereoisomer and thus offers a valuable starting point for further synthetic exploration.

Graphical abstract: Strategy towards the enantioselective synthesis of schiglautone A

Supplementary files

Article information

Article type
Paper
Submitted
28 Mar 2017
Accepted
04 Jul 2017
First published
04 Jul 2017

Org. Biomol. Chem., 2017,15, 6242-6256

Strategy towards the enantioselective synthesis of schiglautone A

C. Le Chapelain, Org. Biomol. Chem., 2017, 15, 6242 DOI: 10.1039/C7OB00766C

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