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Synthesis 2018; 50(05): 1152-1158
DOI: 10.1055/s-0036-1589152
DOI: 10.1055/s-0036-1589152
paper
A Concise and Stereoselective Total Synthesis of Pestalotioprolide C Using Ring-Closing Metathesis
Further Information
Publication History
Received: 12 November 2017
Accepted after revision: 16 November 2017
Publication Date:
20 December 2017 (online)
Abstract
The stereoselective total synthesis of the pestalotioprolide C is disclosed in 13 linear steps in 4% overall yield. The key steps in this approach are a ring-closing-metathesis protocol for the construction of the 14-membered macrolide with E-olefinic bond, a Keck allylation, and a Sharpless kinetic resolution for the installation of desired stereocenters at C4 and C7.
Key words
pestalotioprolide C - 14-membered macrolide - Keck allylation - Sharpless kinetic resolution - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589152.
- Supporting Information
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