This research was supported in part by a Grant-in-Aid for a Scientific Research (B, KAKENHI No. 22390004) from the Japan Society for the Promotion Science. We sincerely thank Dr. Kentaro Okano (Tohoku University) for helpful discussion.
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Communication
Concise Total Synthesis of (−)-Myxalamide A†
Article first published online: 13 JUN 2012
DOI: 10.1002/anie.201203093
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Fujita, K., Matsui, R., Suzuki, T. and Kobayashi, S. (2012), Concise Total Synthesis of (−)-Myxalamide A . Angew. Chem. Int. Ed., 51: 7271–7274. doi: 10.1002/anie.201203093
- †
Publication History
- Issue published online: 11 JUL 2012
- Article first published online: 13 JUN 2012
- Manuscript Received: 23 APR 2012
Funded by
- Japan Society for the Promotion Science
Keywords:
- aldol reaction;
- cross-coupling;
- polyene antibiotics;
- protecting-group-free synthesis;
- total synthesis
The MIDA touch: A concise and highly convergent protecting-group-free total synthesis of (−)-myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O-acetal, together with a one-pot Stille/Suzuki–Miyaura cross-coupling reaction using Burke's N-methyliminodiacetic acid (MIDA) boronate to connect left- and right-hand fragments of the molecule (see scheme).