Parallel Kinetic Resolution Approach to the Cyathane and Cyanthiwigin Diterpenes Using a Cyclopropanation/Cope Rearrangement

✍ Scribed by Laura C. Miller; J. Maina Ndungu; Richmond Sarpong

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 346 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200806154

✦ Synopsis

Abstract

Parallel effort: Stereodivergent parallel kinetic resolution of a racemic mixture of dienes using Davies' [Rh~2~{(S)‐dosp}~4~] or [Rh~2~{(R)‐dosp}~4~] catalysts promotes a tandem vinyl diazoacetate cyclopropanation/Cope rearrangement sequence to afford two diastereomeric, enantioenriched cycloheptadienes, which correspond to the natural antipodes of the title diterpenoids (see scheme).magnified image