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Selective oxidation of lignan compounds by dimethyldioxirane. Diastereoselective opening of asarinin furo-furan skeleton

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
47
Identifiers
DOI: 10.1016/s0040-4039(98)01912-1
Disciplines
  • Chemistry

Abstract

Abstract Asarinin, a furo-furan lignan compound with two benzyl-ethereal carbons of opposite stereochemistry, was monooxidised at a selected centre by DMD to a chiral substituted tetrahydrofuran. Use of a dilute solution of DMD was crucial for the success of the process. The stereochemistry of the product was confirmed by a similar oxidation of sesamin, the C-7′ isomer of asarinin.

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