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Synthesis of a protected C‐11/C‐17 segment of mycinolide‐V
Author(s) -
Ditrich Klaus,
Hoffmann Reinhard W.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900103
Subject(s) - chemistry , iodide , block (permutation group theory) , selectivity , stereochemistry , organic chemistry , catalysis , combinatorics , mathematics
Starting from D ‐ribonolactone, the cyclopentylidene‐protected dihydroxy ester 12 was prepared in five steps. Reaction of its enolate 13 with benzyloxymethyl iodide gave the esters 15 and 16 with modest selectivity. Each of these was converted into the desired mycinolide building block 32 in seven and six steps, respectively.