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A Highly Convergent Total Synthesis of (+)‐Myxovirescine M 2 . Preliminary Communication
Author(s) -
Seebach Dieter,
Maestro Miguel A.,
Sefkow Michael,
Neidlein Axel,
Sternleld Francine,
Adam Geo,
Sommerfeld Thimo
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740846
Subject(s) - chemistry , total synthesis , borane , bromide , hydroxymethyl , reagent , malic acid , nucleophile , stereochemistry , extender , combinatorial chemistry , organic chemistry , citric acid , polyurethane , catalysis
The antibiotic myxovirescine M 2 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 (2 R ,4 S )‐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.