Synthesis 2015; 47(08): 1181-1189
DOI: 10.1055/s-0034-1379984
paper
© Georg Thieme Verlag Stuttgart · New York

The First Stereoselective Synthesis of a Dithiane Derivative of the C18 β-Diketodiene System Proposed for an Active Compound Isolated from Cantharellus cibarius (Chanterelle)

Jacek Grodnera, W. Marek Gołębiewski*a, Michael C. Willisb, James D. Osborneb, Mirosław Gucmaa
  • alnstitute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland   Email: golebiewski@ipo.waw.pl
  • bDepartment of Chemistry, University of Oxford, Chemical Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK   Email: michael.willis@chem.ox.ac.uk
Further Information

Publication History

Received: 02 October 2014

Accepted after revision: 19 December 2014

Publication Date:
27 January 2015 (eFirst)

Abstract

A stereocontrolled synthesis of a thioketal system that is a direct precursor of an active compound isolated from chanterelle was accomplished by using readily available methyl 11-[2-(2-oxoethyl)-1,3-dithian-2-yl]undec-9-ynoate as a key intermediate. The synthesis involves simple and straightforward reactions, such as addition of a lithiated alkyne to an aldehyde, alkyne hydrogenation using nickel boride, alcohol oxidation with Dess–Martin periodinane, and Z-to-E enone isomerization.

Supporting Information