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A stereocontrolled total synthesis of (+,-)-renieramycin A

By Steven Douglas Linton

Abstract

A novel synthetic route via iterative condensations of piperazinedione and substituted benzaldehydes has resulted in the first total synthesis of the complex antibiotic, renieramycin A 1a. Salient features include an acyliminium ion-mediated construction of a diazabicyclo (3.3.1) nonane nucleus, which allows for stereoselective hydrogenation and benzylic oxidation. The stereochemistry of the angelate side chain was unequivocally determined by X-ray crystallographic analysis of the penultimate intermediate, 67b. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI

Topics: Organic chemistry, Pharmaceutical chemistry
Year: 1992
OAI identifier: oai:scholarship.rice.edu:1911/16531
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