Total synthesis of the racemic 3-methyl analogue of the antitumour agent acivicin
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1915-1921
- https://doi.org/10.1039/p19890001915
Abstract
The racemic 3-methyl analogue (19a) of acivicin (1) has been synthesized by a stereorandom route starting with acetonitrile oxide (3) and a novel vinylglycine precursor, ethyl 2-acetoxybut-3-enoate (9). The diastereoisomeric alcohols (11a,b) and azides (14a,b) were separated and used for the synthesis of the individual diastereoisomers of compounds (10), (12), and (15)–(19). The erythro- and threo-diastereoisomers were identified on the basis of their 1H and 13C n.m.r. spectra.Keywords
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