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Synthesis 2015; 47(08): 1181-1189
DOI: 10.1055/s-0034-1379984
DOI: 10.1055/s-0034-1379984
paper
The First Stereoselective Synthesis of a Dithiane Derivative of the C18 β-Diketodiene System Proposed for an Active Compound Isolated from Cantharellus cibarius (Chanterelle)
Further Information
Publication History
Received: 02 October 2014
Accepted after revision: 19 December 2014
Publication Date:
27 January 2015 (online)
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.
Key words
total synthesis - stereoselective synthesis - hydroacylations - cross-coupling - organometallic reagents - thioketalsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379984.
- Supporting Information
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