In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 11, No. 4 ( 2024), p. 1084-1089
Abstract:
Two synthetic approaches to peshawaraquinone, an uncommon and complex naphthoquinone meroterpenoid, are described. Key to the success of these synthetic pathways includes HFIP-promoted metal-free allylation to couple lawsone with allylic alcohols, together with an organo-catalyzed [3 + 2] cycloaddition for constructing the bicyclo[3.2.1] octane core structure. A [2 + 2] photocycloaddition/α-ketol rearrangement sequence was also applied as an alternative approach to peshawaraquinone. Further investigation revealed that natural peshawaraquinone is a racemate.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2024
detail.hit.zdb_id:
2757215-8