Journal
ORGANIC LETTERS
Volume 18, Issue 8, Pages 1752-1755Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00446
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Funding
- BRNS, DAE, Government of India [2011/20/37C/12/BRNS/1731]
- SERB, DST, Government of India [SB/FT/CS-54/2011]
- CSIR, New Delhi
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A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)(2) and Bi(OTf)(3) in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).
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