ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The antibiotic myxovirescine M2 was synthesized from seven building blocks (1-7, Scheme 1), with the following chiral starting materials being employed: (S)-malic acid, (+)-D-ribonolactone, (S)-2-(hydroxymethyl)butanoate, and (2R,4S)-5-hydroxy-2,4-dimethylpenLanoate. Three new nucleophilic reagents, 8-10, for C-C bond formation have been used. The key steps of the synthesis are: a Suzuki coupling between an alkyl borane and a vinyl bromide (4 + 12e → 13), a Julia olefinalion (14 + 17 → 18), and a Yamaguchi macrolactonizalion to form the 28-membered lactone (18 → 19), This extremely convergenl synthetic approach will allow the preparation of a number of the 31 known myxovirescine molecules.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740846
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