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Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation
Author(s) -
Drew Michael G. B.,
Harwood Laurence M.,
MacíasSánchez Antonio J.,
Scott Richard,
Thomas R. M.,
Uguen Daniel
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(20010618)40:12<2311::aid-anie2311>3.0.co;2-t
Subject(s) - cyclopropanation , carbenoid , chemistry , substituent , lithium (medication) , ether , silyl ether , stereochemistry , medicinal chemistry , organic chemistry , catalysis , silylation , rhodium , biology , endocrinology
The diastereocomplementarity of halo‐ and alkylcarbenes (paths a and b, respectively) was shown in the cyclopropanation reaction of 1 . The conversion of 1 into 7,7‐dimethylbicyclo[4.1.0]heptan‐1,2‐diols (±)‐ 2 and (±)‐ 3 represents an important transformation in a synthetic strategy towards phorbol derivatives. TBDMS= tert ‐butyldimethylsilyl.