Synthesis of Furocoumarin-Type Potential Intercalative Alkylating and Oxidizing Agents of DNA Through Dimethyldioxirane Epoxidation of Imperatorin and Its Derivatives
✍ Scribed by Abou-Elzahab, Mohamed M. ;Adam, Waldemar ;Saha-Möller, Chantu R.
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 315 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Epoxidation of imperatorin (1a) by dimethyldioxirane (DMD) affords the natural product prangenin (2a) in excellent yield. Similarly, alloimperatorin (1b) and its methyl and acetate derivatives 1b–d are epoxidized with DMD to give the corresponding epoxides 2b–d in quantitative yields. Furthermore, the reaction of the imperatorin allylic hydroperoxide 1e with DMD, and for comparison with m‐chloroperbenzoic acid (CPBA), yields the diastereomeric epoxy hydroperoxides (R*,S*)‐ and (R*,R*)‐2e in low but of opposite diastereoselectivity. Thus, for DMD the (R*,S*)/(R*,R*‐2e ratio is 56:44 and for CPBA 40:60.