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Manganese(III)-Promoted Tandem Oxidation and Cyclization of β-Keto Ester Derivatives of Terpenoids

✍ Scribed by Zhilong Li; Heejung Jung; Mira Park; Myoung Soo Lah; Sangho Koo

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 240 KB
Volume: 353
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.201100215

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✦ Synopsis

Abstract

A new type of terpenoid cyclization directed by a β‐keto ester moiety has been developed, which proceeded by manganese(III)‐initiated oxidation of the β‐keto ester, followed by an intramolecular hetero Diels–Alder reaction with the terpenoid chain. This reaction produces polycyclic dihydropyrans in high yields and stereoselectivities under mild conditions.

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