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Transannular Radical Cascade as an Approach to the Diastereoselective Synthesis of Linear Triquinane
Author(s) -
Dhimane AnneLise,
Aïssa Christophe,
Malacria Max
Publication year - 2002
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(20020902)41:17<3284::aid-anie3284>3.0.co;2-z
Subject(s) - cascade , scheme (mathematics) , chemistry , computer science , stereochemistry , natural (archaeology) , combinatorial chemistry , mathematics , biology , chromatography , mathematical analysis , paleontology
A completely selective entry to the triquinane family is described from a highly strained cycloundecadienyne framework, simply by choosing the correct propargylic position for the radical trigger (see scheme; A: natural protoilludane, B: linear triquinane, BMDMS=(bromomethyl)dimethylsilyl, TBS= tert ‐butyldimethylsilyl).