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Total Syntheses of Cyanthiwigins B, F, and G
Author(s) -
Enquist John A.,
Virgil Scott C.,
Stoltz Brian M.
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.201100425
Subject(s) - stereocenter , aldehyde , tandem , olefin fiber , chemistry , alkylation , total synthesis , combinatorial chemistry , stereochemistry , selectivity , olefin metathesis , metathesis , catalysis , enantioselective synthesis , organic chemistry , materials science , polymer , composite material , polymerization
Abstract A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring‐closing cross‐metathesis reaction, and an aldehyde‐olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.