Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation

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 de...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2001-06, Vol.40 (12), p.2311-2313
Main Authors: Drew, Michael G. B., Harwood, Laurence M., Macías-Sánchez, Antonio J., Scott, Richard, Thomas, R. M., Uguen, Daniel
Format: Article
Language:English
Subjects:
carbenoids
cyclopropanations
diastereoselectivity
enol ethers
synthetic methods
Online Access:Get full text
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010618)40:12<2311::AID-ANIE2311>3.0.CO;2-T