We thank Prof. Fumio Sugawara (Tokyo University of Science) for providing a sample and the spectral copies of natural pestalotiopsin A. This work was supported by a Grant-in-Aid for Young Scientists (B) from MEXT and the Astellas Pharma Award in Synthetic Organic Chemistry (Japan).
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Communication
Total Synthesis of (−)-Pestalotiopsin A†
Article first published online: 25 MAR 2008
DOI: 10.1002/anie.200800253
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Takao, K.-i., Hayakawa, N., Yamada, R., Yamaguchi, T., Morita, U., Kawasaki, S. and Tadano, K.-i. (2008), Total Synthesis of (−)-Pestalotiopsin A. Angew. Chem. Int. Ed., 47: 3426–3429. doi: 10.1002/anie.200800253
- †
Publication History
- Issue published online: 14 APR 2008
- Article first published online: 25 MAR 2008
- Manuscript Received: 17 JAN 2008
Funded by
- MEXT
Keywords:
- chiral auxiliaries;
- cyclization;
- cycloaddition;
- synthesis design
A big “+”: The total synthesis of (−)-pestalotiopsin A has been achieved, thereby establishing the absolute stereochemistry of natural (+)-pestalotiopsin A (see scheme). The synthesis features a [2+2] cycloaddition, an aldol reaction, and an intramolecular Nozaki–Hiyama–Kishi reaction to construct the (E)-cyclononene ring.