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Synthesis 2017; 49(13): 2939-2942
DOI: 10.1055/s-0036-1588999
DOI: 10.1055/s-0036-1588999
paper
A Short Asymmetric Synthesis of Sauropunols A–D
Supported by: This work was supported by Slovak Grant Agencies (VEGA No. 1/0488/14, APVV-14-0147 and ASFU, Bratislava, ITMS project No. 26240120025).Further Information
Publication History
Received: 24 February 2017
Accepted after revision: 21 March 2017
Publication Date:
18 April 2017 (online)
Abstract
A short and efficient asymmetric synthesis of natural sauropunols A, B, and C/D has been accomplished in 6 steps from divinylcarbinol with overall yield of 19%, 7% and 32%, respectively. The key synthetic steps include effective Sharpless asymmetric epoxidation of penta-1,4-dien-3-ol and a highly diastereoselective Pd-catalysed oxycarbonylation of pentene-1,2,3-triol. The structures of sauropunols A and B have been confirmed.
Key words
total synthesis - natural compounds - asymmetric synthesis - palladium - carbonylation - Sauropus rostratusSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588999.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0091th.
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