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  • Total synthesis of (±)-cavicularin: control of pyrone Diels-Alder regiochemistry using isomeric vinyl sulfones.

Total synthesis of (±)-cavicularin: control of pyrone Diels-Alder regiochemistry using isomeric vinyl sulfones.

Organic letters (2013-01-11)
Peng Zhao, Christopher M Beaudry
ABSTRACT

An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Divinyl sulfone, contains hydroquinone as inhibitor, ≥96%