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Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23‐Dihydroavermectin B 1b Aglycone
Author(s) -
Frei Bruno,
Huxley Philip,
Maienfisch Peter,
Mereyala Hari Babu,
Rist Günther,
O'Sullivan Anthony C.
Publication year - 1990
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.19900730713
Subject(s) - chemistry , aglycone , allylic rearrangement , stereochemistry , avermectin , organic chemistry , catalysis , glycoside , medicine , anatomy
The synthesis of several configurationally defined hydroxymilbemycin derivatives is described. One of these allylic alcohols is the known 5‐ O ‐[( tert ‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐ O ‐[( tert ‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B 1b , aglycone; 15D ), the synthesis of which represents LI conversion of the milbemycin to the avermectin series of natural products. The configurations at C(13), C(14), and C(15) of the new milbemycin derivatives were determined by NMR experiments and force‐field calculations.