Semisynthesis of Ingenol 3-Angelate (PEP005): Efficient Stereoconservative Angeloylation of Alcohols

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...

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Bibliographic Details
Published inSynlett no. 18; pp. 2647 - 2652
Main Authors Liang, Xifu, Grue-Sorensen, Gunnar, Petersen, Anders Klarskov, Hogberg, Thomas
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 13.11.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SEEDS
MEBUTATE GEL
ACID
ingenol 3-angelate
isomerization
tiglate
ANALOGS
ingenol
angeloylation
CHEMISTRY
ANGELATE
PEP005
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1317415