A Short Asymmetric Synthesis of Sauropunols A–D

Author:

Gracza Tibor1,Markovič Martin12,Koóš Peter12

Affiliation:

1. Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology

2. Georganics Ltd., Koreničova 1, 811 03 Bratislava

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.

Funder

This work was supported by Slovak Grant Agencies

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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