Support studies for the conversion of actinobolin into bactobolin
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 731-738
- https://doi.org/10.1039/p19900000731
Abstract
Strategies for the final steps in a synthesis of bactobolin have been examined on substrates obtained by retrograde transformations of actinobilin. It is shown that α-acetamido ketones react with LiCHCl2 from the Re face thereby generating the C-5 configuration required for bactobolin. However, the transformations involved are highly substrate specific. The reasons for this sensitivity are not apparent, but they indicate the need for caution in laying plans for the finals steps of a synthesis.This publication has 4 references indexed in Scilit:
- .pi.-Facial selection in intermolecular Diels-Alder reactions: total syntheses of (+)-actinobolin and (+)-5,6,10-triepiactinobolinJournal of the American Chemical Society, 1987
- An approach to the synthesis of bactobolin and the total synthesis of N-acetylactinobolamine: some remarkably stable hemiacetalsThe Journal of Organic Chemistry, 1987
- Controlled reduction and oxidation of actinobolinTetrahedron, 1986
- Adsorption of the antibiotic actinobolin by hydroxyapatiteArchives of Oral Biology, 1980