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Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6‐ cis ‐Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins
Author(s) -
Lu Ji,
Song Zhenlei,
Zhang Yuebao,
Gan Zubao,
Li Hongze
Publication year - 2012
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/anie.201201323
Subject(s) - vinylsilane , prins reaction , silylation , ring (chemistry) , aldehyde , stereochemistry , chemistry , organic chemistry , catalysis
Prins Charming : Prins cyclization of a bis(silyl) homoallylic alcohol with an aldehyde shows excellent cis and Z selectivity to form tetrahydropyrans containing a geometrically defined exocyclic vinylsilane. This reaction was used as the key step in the synthesis of ring B of the bryostatins.
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