ASYMMETRIC TOTAL SYNTHESIS OF INDOLMYCIN
- 5 February 1980
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 9 (2), 163-166
- https://doi.org/10.1246/cl.1980.163
Abstract
An asymmetric total synthesis of indolmycin was achieved via a key intermediate, α-indolmycenic acid ester. The ester was obtained by oxygenation of methyl (S)-3-(3-indolyl)butanoate which was prepared by asymmetric synthesis utilizing (2R,3S)-3,4-dimethyl-2-phenylperhydro-l,4-oxazepine-5,7-dione. (2S,3R)-N-[2-Hydroxy-3-(3-indolyl)-butanoyl]-N′-methylthiourea prepared from α-indolmycenic acid ester was treated with 2-chlorobenzoxazolium salt to give indolmycin in 93% optical purity.Keywords
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