Synthesis of (+)-Omphadiol and (+)-Pyxidatol C

authored by

Gowrisankar Parthasarathy, Ulrike Eggert, Markus Kalesse

Abstract

The synthesis of (+)-omphadiol and (+)-pyxidatol C was achieved through two independent strategies. For the synthesis of (+)-omphadiol, dicyclopentadienone was used as the workbench on which the three contiguous stereocenters of the cyclopentane could be introduced selectively. These include a tertiary alcohol and a selective protonation of an enolate. A ring-closing metathesis and a cyclopropanation concluded the synthesis. For the synthesis of pyxidatol C, we used the epoxide derived from (R)-linalool that was transformed to cyclopentane 23. After chain extension, another ring-closing metathesis followed by oxidation state changes and finally a cyclopropanation led to (+)-pyxidatol C.

Organisation(s)

Institute of Organic Chemistry
Centre of Biomolecular Drug Research (BMWZ)

Type

Article

Journal

Organic letters

Volume

18

Pages

2320-2322

No. of pages

3

ISSN

1523-7060

Publication date

06.05.2016

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Biochemistry, Physical and Theoretical Chemistry, Organic Chemistry

Electronic version(s)

https://doi.org/10.1021/acs.orglett.6b00814 (Access: Closed)
https://doi.org/10.1021/acs.orglett.6b01361 (Access: Closed)