Enantioselective Syntheses of (+)- and (−)-Blastmycinolactol

(−)-Blastmycinolactol ( 1b) has been prepared in an enantioselective fashion from acetylenic acid 5 by a three step sequence involving debenzylation-lactonization, hydration with concurrent C 3-epimerization, and Baeyer-Villiger oxidation accompanied by ester cleavage. Acylation of 1b with isovalery...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 38; pp. 6621 - 6624
Main Authors Jacobi, Peter A., Herradura, Prudencio
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.09.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
ALDOL REACTIONS
ASYMMETRIC-SYNTHESIS
(+)-BLASTMYCINONE
ACID
LACTONES
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Summary:(−)-Blastmycinolactol ( 1b) has been prepared in an enantioselective fashion from acetylenic acid 5 by a three step sequence involving debenzylation-lactonization, hydration with concurrent C 3-epimerization, and Baeyer-Villiger oxidation accompanied by ester cleavage. Acylation of 1b with isovaleryl chloride then afforded (+)-blastmycinone ( 1a) in excellent overall yield. © 1997 Elsevier Science Ltd.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01533-5