Jump to main content
Jump to site search

Issue 28, 2012
Previous Article Next Article

A convergent stereocontrolled total synthesis of (−)-terpestacin

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 May 2012, accepted on 30 May 2012 and first published on 13 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25940K
Citation: Org. Biomol. Chem., 2012,10, 5452-5455
  •   Request permissions

    A convergent stereocontrolled total synthesis of (−)-terpestacin

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

Search articles by author

Spotlight

Advertisements