Issue 28, 2012

A convergent stereocontrolled total synthesis of (−)-terpestacin

Abstract

A stereocontrolled total synthesis of (−)-terpestacin has been achieved starting from (R)-(−)-carvone as a chiral pool and (E,E)-farnesol via a highly convergent approach. Thus, (R)-(−)-carvone was transformed into the cyclopentanone segment through a series of high yielding operations with the proper setup of all the stereochemical centers while (E,E)-farnesol was converted into the other requisite building block via a series of high yielding reactions. The cyclopentanone intermediate was both selectively enolized and alkylated at room temperature to yield the desired coupling product, which provided the natural product upon further transformations.

Graphical abstract: A convergent stereocontrolled total synthesis of (−)-terpestacin

Supplementary files

Article information

Article type
Paper
Submitted
16 May 2012
Accepted
30 May 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 5452-5455

A convergent stereocontrolled total synthesis of (−)-terpestacin

Y. Jin and F. G. Qiu, Org. Biomol. Chem., 2012, 10, 5452 DOI: 10.1039/C2OB25940K

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