Issues of Orthogonality and Stabilty: Synthesis of the Densely Functionalized Heterocyclic Ring System of the Antitumor Agents Azinomycins A and B

Robert S. Coleman

doi:10.1055/s-1998-1853

Synlett 1998; 1998(10): 1031-1039
DOI: 10.1055/s-1998-1853

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Issues of Orthogonality and Stabilty: Synthesis of the Densely Functionalized Heterocyclic Ring System of the Antitumor Agents Azinomycins A and B

Robert S. Coleman^*

^*Department of Chemistry, The Ohio State University, 100 West 18^th Ave., Columbus, Ohio 43210, USA; Fax 614-292-4647; E-mail: coleman@chemistry.ohio-state-edu

Abstract

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The aziridino[1,2-a]pyrrolidine ring system of azinomycin A and B is a key substructure of the agents responsible for DNA alkylation. Work on the synthesis of this key substructure of the agents is described, and is focused on stereoselectivity in introduction of the stereogenic elements including the tetrasubstituted double bond of the dehydroamino acid. Issues surrounding the selectively acetylated C12/C13 diol system, specifically with deprotection of a penultimate C12 ether to ester, are discussed in the context of a total synthesis and with respect to stability of the natural agents.

antitumor agents - azinomycins A and B - aziridine

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