Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation

Andrew S. Kende, Robert J. DeVita

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Reaction of the dianion (5) derived from an acylaminomalonic ester with S-(-)-MOM lactate (6) yields β-hydroxylactams 7 and 8 in a 2:1 ratio. Deprotection and lactonization of 7, followed by saponification and 2 step carboxyl reduction efficiently produces the fused bicyclic lactam-lactone 12, a chiral model of the antitumor antibiotic neooxazolomycm 1.

Original languageEnglish
Pages (from-to)2521-2524
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number21
DOIs
StatePublished - 1988
Externally publishedYes

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