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Total Synthesis of (+)‐(2′ S ,3′ R )‐Zoapatanol Exploiting the B ‐Alkyl Suzuki Reaction and the Nucleophilic Potential of the Sulfinyl Group
Author(s) -
Raghavan Sadagopan,
Sudheer Babu Vaddela
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003666
Subject(s) - stereocenter , alkene , stereoselectivity , chemistry , intramolecular force , nucleophile , alkyl , stereochemistry , total synthesis , ring (chemistry) , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis
Abstract A stereoselective synthesis of the diterpenoid oxepane (+)‐zoapatanol is described. The key steps include a B ‐alkyl Suzuki cross‐coupling reaction for the stereoselective synthesis of trisubstituted alkenes, creation of the two stereogenic centers on the oxepane ring by heterofunctionalization of an alkene through substrate control exploiting the nucleophilic potential of an intramolecular sulfinyl group, and transformation of a β‐hydroxy sulfoxide into a terminal alkene.