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Total Synthesis of (+)‐Pyrenolide D
Author(s) -
Engstrom Kenneth M.,
Mendoza Mario R.,
NavarroVillalobos Mauricio,
Gin David Y.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010316)40:6<1128::aid-anie11280>3.0.co;2-j
Subject(s) - total synthesis , stereoselectivity , stereochemistry , chemistry , contraction (grammar) , oxidative phosphorylation , ring (chemistry) , combinatorial chemistry , biology , organic chemistry , biochemistry , catalysis , endocrinology
The direct stereoselective I III ‐mediated oxidative ring contraction of a protected 6‐deoxy‐ D ‐gulal substrate to form a highly functionalized tetrahydrofurfural intermediate is a key step in the first total synthesis of (+)‐pyrenolide D (see scheme; R = TBS = tert ‐butyldimethylsilyl).