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Synthesis 2017; 49(13): 2939-2942
DOI: 10.1055/s-0036-1588999
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© Georg Thieme Verlag Stuttgart · New York

A Short Asymmetric Synthesis of Sauropunols A–D

Martin Markovič
a   Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Email: tibor.gracza@stuba.sk
b   Georganics Ltd., Koreničova 1, 811 03 Bratislava, Slovakia
,
Peter Koóš
a   Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Email: tibor.gracza@stuba.sk
b   Georganics Ltd., Koreničova 1, 811 03 Bratislava, Slovakia
,
Tibor Gracza*
a   Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Email: tibor.gracza@stuba.sk
› Author AffiliationsSupported 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)

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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 rostratus

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588999.
  • Supporting Information

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.

  • Primary Data
 

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