Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.
Organic & Biomolecular Chemistry2003Vol. 1(23), pp. 4173–4208
Citations Over TimeTop 10% of 2003 papers
Gerald Pattenden, Miguel A. González, Paul B. Little, David S. Millan, Alleyn T. Plowright, James A. Tornos, Tao Ye
Abstract
A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.
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