We thank Dr. D.-H. Huang and Dr. R. Chadha for spectroscopic and X-ray crystallographic assistance, respectively, and Dr. G. Siuzdak and Doris Tan for mass spectrometric assistance. Financial support for this work was provided by A*STAR, Singapore, the Skaggs Institute for Chemical Research, the National Institutes of Health (grant AI 055475-09), and the National Science Foundation (Graduate Research Fellowship to C.R.H.H.).
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Communication
An Expedient Synthesis of a Functionalized Core Structure of Bielschowskysin†
Article first published online: 26 APR 2011
DOI: 10.1002/anie.201101360
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Nicolaou, K. C., Adsool, V. A. and Hale, C. R. H. (2011), An Expedient Synthesis of a Functionalized Core Structure of Bielschowskysin. Angew. Chem. Int. Ed., 50: 5149–5152. doi: 10.1002/anie.201101360
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Publication History
- Issue published online: 16 MAY 2011
- Article first published online: 26 APR 2011
- Manuscript Received: 23 FEB 2011
Funded by
- National Institutes of Health. Grant Number: AI 055475-09
- National Science Foundation
Keywords:
- antimalarial agents;
- cytotoxic agents;
- natural products;
- photocycloaddition
Photons in action: Cascade sequences, brevity, and efficiency are the hallmarks of the synthesis of a functionalized tricyclo[9.3.0.0]tetradecane ring system of the marine natural product bielschowskysin. The synthesis is achieved in five steps, with the key step being an exquisite intramolecular [2+2] photocycloaddition of a macrocyclic precursor (see scheme).