First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the “Skipped” ( Z )‐Enediyne Moiety by Oxidative Coupling of Homopropargylphosphonium Ylide | Zendy

Gung Benjamin W. | Zendy; Omollo Ann O. | Zendy

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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)

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