Synthesis based on cyclohexadienes. Part 15. Total synthesis of (±)-prezizaene, (±)-prezizanol and (±)-jinkohol II

Selvakumar, Natesan and Rao, Subba GSR (1994) Synthesis based on cyclohexadienes. Part 15. Total synthesis of (±)-prezizaene, (±)-prezizanol and (±)-jinkohol II. In: Perkin Transactions 1 (21). 3217-3223 .

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Abstract

A new methodology for the synthesis of the complex ring system tricyclo[6.2.1.0(1.5)]undecane. present in the zizaene group of sesquiterpenes, is described. Acid-catalysed rearrangement of the endo alcohol 20 afforded the enone 12, which was transformed stereoselectively into the key intermediate. (+/-)-norprezizanone 10. The features of the synthesis are the transformation of a bicycle[2.2.2] octane framework into a bicycle[3.2.1] octane system by an acid-catalysed rearrangement and a stereoselective conjugate addition of a methyl group on an alpha,beta-unsaturated keto ester at -100 degrees C. Norprezizanone was converted into the sesquiterpenes (+/-)-prezizanol 5 and(+/-)-prezizaene 4. The first total synthesis of (+/-)-jinkohol II 6 is also presented.

Item Type:	Journal Article
Publication:	Perkin Transactions 1
Publisher:	Royal society of chemistry
Additional Information:	Copyright of artical belongs to Royal society of chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	18 Apr 2011 05:27
Last Modified:	18 Apr 2011 05:27
URI:	http://eprints.iisc.ac.in/id/eprint/36860

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