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Synthesis 2017; 49(11): 2483-2487
DOI: 10.1055/s-0036-1588972
DOI: 10.1055/s-0036-1588972
paper
First Stereoselective Synthesis of (6R,7R,8S)-8-Chlorogoniodiol
Weitere Informationen
Publikationsverlauf
Received: 04. November 2016
Accepted after revision: 28. Februar 2017
Publikationsdatum:
17. März 2017 (online)
Abstract
A stereoselective synthesis of (6R,7R,8S)-8-chlorogoniodiol has been achieved in a linear sequence of 12 steps and 19.8% overall yield from cinnamyl alcohol. The key steps include Sharpless asymmetric epoxidation, regioselective ring opening of epoxide, indium-mediated Barbier allylation, and Still–Gennari olefination.
Key words
first total synthesis - Sharpless epoxidation - indium-mediated Barbier allylation - Still–Gennari olefinationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588972.
- Supporting Information
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