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- Title
Total Synthesis of (+)-Dendrowardol C.
- Authors
Wolleb, Helene; Carreira, Erick M.
- Abstract
The first total synthesis of the tetracyclic sesquiterpenoid (+)-dendrowardol C is described. It relies on an intramolecular aldol reaction to forge the central bicyclic scaffold and subsequent cyclobutane formation by cyclization of a γ-triflyloxy ketone. Key is the treatment of the latter with lithium naphthalenide. Finally, the diastereoselective hydroboration of a 1,1-disubstituted double bond is enabled by a chiral CoI catalyst.
- Subjects
ALDOLS; CYCLOBUTANE; STEREOSELECTIVE reactions; HYDROBORATION; DOUBLE bonds; CHEMICAL synthesis
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 36, p11030
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201705809