Affiliation:
1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
2. Center for Instrumental Analysis, Tokyo University of Pharmacy and Life Sciences
Abstract
An efficient installation of a 3,7-dimethylocta-2,6-dien-1-yl (geranyl or neryl) side chain at the C(1) position of a xanthone core by utilizing an anion-accelerated aromatic oxy-Cope rearrangement is described. Experiments revealed that this uncommon rearrangement takes place in a stereospecific manner through a chair-like transition-state structure. An application to the syntheses of the natural xanthone fuscaxanthone F, possessing a geranyl side chain, and its neryl analogue is also described.
Funder
Ministry of Education, Culture, Sports, Science and Technology
Japan Society for the Promotion of Science
Cited by
5 articles.
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