NIS–PPh3: A Selective Reagent for the Spiroannulation of o‑Allyl Phenols. Total Synthesis of Corallidictyal D

Treatment of o-allyl phenols with catalytic NIS–PPh3 affords the corresponding spiro­dihydro­benzo­furan derivatives in high yield with high regio- and total stereoselectivity under mild conditions. These results were utilized to achieve the first total synthesis of the protein kinase C inhibitor co...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-09, Vol.78 (18), p.9196-9204
Main Authors: Cano, M. José, Bouanou, Hanane, Tapia, Rubén, Alvarez, Esteban, Alvarez-Manzaneda, Ramón, Chahboun, Rachid, Alvarez-Manzaneda, Enrique
Format: Article
Language:English
Subjects:
Indicators and Reagents - chemistry
Molecular Conformation
Phenols - chemistry
Phosphines - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Succinimides - chemistry
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Summary:Treatment of o-allyl phenols with catalytic NIS–PPh3 affords the corresponding spiro­dihydro­benzo­furan derivatives in high yield with high regio- and total stereoselectivity under mild conditions. These results were utilized to achieve the first total synthesis of the protein kinase C inhibitor corallidictyal D starting from α-ionone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4014047