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Synlett 2012; 23(18): 2647-2652
DOI: 10.1055/s-0032-1317415
DOI: 10.1055/s-0032-1317415
letter
Semisynthesis of Ingenol 3-Angelate (PEP005): Efficient Stereoconservative Angeloylation of Alcohols
Further Information
Publication History
Received: 20 August 2012
Accepted: 17 September 2012
Publication Date:
18 October 2012 (online)
Dedicated to the memory of Professor Horst Prinzbach
Abstract
A high-yielding method was developed for the preparation of ingenol 3-angelate (PEP005, ingenol mebutate) via the corresponding 5,20-acetonide without concomitant isomerization of the angelate (Z-form) to the corresponding tiglate (E-form). The general scope of the stereoconservative esterification method was further evaluated on several different alcohols, giving the angelates in up to quantitative yield without isomerization to the tiglate.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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