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First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the “Skipped” ( Z )‐Enediyne Moiety by Oxidative Coupling of Homopropargylphosphonium Ylide
Author(s) -
Gung Benjamin W.,
Omollo Ann O.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800593
Subject(s) - chemistry , enediyne , enantiomer , total synthesis , natural product , moiety , oxidative coupling of methane , stereochemistry , ylide , absolute configuration , kinetic resolution , enantioselective synthesis , organic chemistry , methane , catalysis
Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C 2 symmetry. The first total synthesis of both enantiomers of the potent anti‐cancer natural product (+)‐ and (–)‐dideoxypetrosynol A is reported. The key step is an oxidative coupling of a homopropargylphosphonium ylide to prepare the “skipped” ( Z )‐enediyne moiety. The natural dideoxypetrosynol A was isolated as a racemic mixture as shown in structure 1 . The absolute configurations of the chiral centers are established for the (+)‐ and (–)‐enantiomers using Burgess' enzymatic resolution procedure with Pseudomonas AK lipase. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)