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

verfasst von

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.

Organisationseinheit(en)

Institut für Organische Chemie
Zentrum für Biomolekulare Wirkstoffe (BMWZ)

Typ

Artikel

Journal

Organic letters

Band

18

Seiten

2320-2322

Anzahl der Seiten

3

ISSN

1523-7060

Publikationsdatum

06.05.2016

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Biochemie, Physikalische und Theoretische Chemie, Organische Chemie

Elektronische Version(en)

https://doi.org/10.1021/acs.orglett.6b00814 (Zugang: Geschlossen)
https://doi.org/10.1021/acs.orglett.6b01361 (Zugang: Geschlossen)