Efficient Synthesis of the D-Ring Fragment of Cobyric Acid
- 9 September 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (20) , 3139-3141
- https://doi.org/10.1021/ol006337n
Abstract
The synthesis of a highly functionalized 4,5-dihydro-3H-pyrrol, namely, the D-ring fragment 5a of cobyric acid (1), is described in this letter. A very efficient assembly to 5a involves CBS-reduction of 10, a [2,3] Wittig−Still rearrangement, and a stereoselective Michael addition to a nitro olefin.Keywords
This publication has 17 references indexed in Scilit:
- Studies on Corrin Synthesis. A Solution to the Introduction of Meso SubstituentsThe Journal of Organic Chemistry, 1999
- Stereocontrolled Synthesis of a Nonracemic Vitamin B12 A−B-SemicorrinJournal of the American Chemical Society, 1997
- A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep synthesesJournal of the American Chemical Society, 1987
- Studies on the synthesis of vitamin B12. 4Journal of the American Chemical Society, 1986
- Synthetic studies relevant to biosynthetic research on vitamin B12. Part 1. Syntheses of C-methylated chlorins based on 1-pyrrolines (3,4-dihydropyrroles)Journal of the Chemical Society, Perkin Transactions 1, 1984
- A highly stereoselective synthesis of Z-trisubstituted olefins via [2,3]-sigmatropic rearrangement. Preference for a pseudoaxially substituted transition stateJournal of the American Chemical Society, 1978
- The total synthesis of vitamin B12Pure and Applied Chemistry, 1973
- Recent advances in the chemistry of natural productsPure and Applied Chemistry, 1971
- Recent advances in the chemistry of natural productsPure and Applied Chemistry, 1968
- Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJournal of the American Chemical Society, 1967