Synthesis 2005(19): 3398-3404  
DOI: 10.1055/s-2005-918485
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Tricyclic Core of the Marine Natural Product Labiatin A

J. Stephen Clark*a, Carl A. Baxtera, José L. Castrob
a School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
b Merck Sharp and Dohme, Neuroscience Research Centre, Terlings Park, Harlow, Essex CM20 2QR, UK
Fax: +44(115)9513564; e-Mail: j.s.clark@nottingham.ac.uk;
Further Information

Publication History

Received 9 September 2005
Publication Date:
14 November 2005 (online)

Abstract

A synthetic route to a model of the tricyclic core of labiatin A is described. Two catalytic metal carbenoid reactions, C-H insertion and oxonium ylide generation with subsequent [2,3]-sigmatropic rearrangement, have been used to assemble the tricyclic system in an efficient and stereoselective manner.