Synthesis of Furocoumarin‐Type Potential Intercalative Alkylating and Oxidizing Agents of DNA Through Dimethyldioxirane Epoxidation of Imperatorin and Its Derivatives | Zendy

AbouElzahab Mohamed M. | Zendy; Adam Waldemar | Zendy; SahaMöller Chantu R. | Zendy

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Synthesis of Furocoumarin‐Type Potential Intercalative Alkylating and Oxidizing Agents of DNA Through Dimethyldioxirane Epoxidation of Imperatorin and Its Derivatives

Author(s) -

AbouElzahab Mohamed M.,

Adam Waldemar,

SahaMöller Chantu R.

Publication year - 1992

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.1992199201123

Subject(s) - dimethyldioxirane , chemistry , furocoumarin , imperatorin , oxidizing agent , organic chemistry , terpene , combinatorial chemistry , dna , biochemistry , high performance liquid chromatography

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.

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