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Oxidation of α,β‐Unsaturated Esters and Lactones with Selenium Dioxide to γ‐Oxo or γ‐Hydroxy Derivatives; Synthesis of (±)‐A 26771 B and Norpyrenophorin
Author(s) -
Bestmann Hans Jürgen,
Schobert Rainer
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198507911
Subject(s) - moiety , selenium , chemistry , lactone , stereochemistry , medicinal chemistry , organic chemistry
The γ‐oxo α,β‐unsaturated lactone moiety COCHCHCOO , which occurs in many macrolide antibiotics, can be synthesized by multicomponent reaction (see previous communication) and oxidation of the lactones thus obtained with SeO 2 . An example is norpyrenophorin 1. The Oxidation with SeO 2 /3% H 2 O yields γ‐hydroxy derivatives.