Issue 22, 2012

Stereoselective synthesis of (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

Abstract

A stereoselective synthesis of (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dötz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet–Spengler reaction to install the 1,3-dimethylpyran moiety.

Graphical abstract: Stereoselective synthesis of (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

Supplementary files

Article information

Article type
Paper
Submitted
01 Mar 2012
Accepted
23 Mar 2012
First published
27 Mar 2012

Org. Biomol. Chem., 2012,10, 4462-4466

Stereoselective synthesis of (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

R. A. Fernandes, A. B. Ingle and V. P. Chavan, Org. Biomol. Chem., 2012, 10, 4462 DOI: 10.1039/C2OB25453K

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