First total synthesis of (+/-)-taxifolial a and (+/-)-iso-caulerpenyne

L Commeiras; M Santelli; J L Parrain

doi:10.1021/ol015903r

First total synthesis of (+/-)-taxifolial a and (+/-)-iso-caulerpenyne

Org Lett. 2001 May 31;3(11):1713-5. doi: 10.1021/ol015903r.

Authors

L Commeiras¹, M Santelli, J L Parrain

Affiliation

¹ Laboratoire de Synthèse Organique associé au CNRS (UMR 6009), Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.

PMID: 11405693
DOI: 10.1021/ol015903r

Abstract

The first synthesis of (+/-)-taxifolial A and iso-caulerpenyne was accomplished. The key steps in the sequence are (1) the stereoselective assembly of a vinyltin derived from butynediol and a functionalized aldehyde and (2) the construction of the dienyne moiety via a Stille cross-coupling.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemical synthesis*
Alkenes / chemical synthesis*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Marine Toxins / chemical synthesis*
Organotin Compounds / chemistry
Seaweed / chemistry
Sesquiterpenes / chemical synthesis*
Stereoisomerism

Substances

Aldehydes
Alkenes
Indicators and Reagents
Marine Toxins
Organotin Compounds
Sesquiterpenes
taxifolial A
caulerpenyne