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The work was supported by the Welch Foundation (A-1280) and NSF (CHE-0809747, partial). We thank Morgan Shirley for technical assistance and Mikail Abbasov for performing calculations and creating the graphic for the cover of this Issue. We thank Prof. Zheng and Prof. Shen for providing the spectroscopic data of natural omphadiol.
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Communication
Total Synthesis of (+)-Omphadiol†
Article first published online: 14 JUL 2011
DOI: 10.1002/anie.201102289
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Liu, G. and Romo, D. (2011), Total Synthesis of (+)-Omphadiol. Angew. Chem. Int. Ed., 50: 7537–7540. doi: 10.1002/anie.201102289
- †
Publication History
- Issue published online: 5 AUG 2011
- Article first published online: 14 JUL 2011
- Manuscript Received: 1 APR 2011
Funded by
- Welch Foundation. Grant Number: A-1280
- NSF. Grant Number: CHE-0809747
Keywords:
- asymmetric synthesis;
- cyclopropanation;
- natural products;
- protecting group free;
- terpenoids
A smooth transition from (R)-carvone to a β-lactone and then to (+)-omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 % overall yield. All six contiguous stereogenic centers were introduced in a highly diastereoselective manner. Key steps include a nucleophile-promoted aldol lactonization, a single-pot, sequential intra-/intermolecular dialkylation, a tandem olefin isomerization/RCM, and a cyclopropanation with unusual facial selectivity.