Journal of Organic Chemistry p. 3274 - 3278 (1982)
Update date:2022-08-04
Topics:
Janssen, Cornelus G. M.
Godefroi, Erik F.
An efficient three-step strategy into resin acid type systems III and their cis isomers VI is presented.As illustrated by five exampels, the method involves geranylation of sulfones 7a-c and nerylation of 7a,b to 8a-c and 9a,b, respectively.Subsequent FSO3H-SO2-promoted polyene cyclizations proceed stereospecifically and with asymmetric induction to produce epimeric diastereomers 10a-c/11a-c and 12a,b/13a,b in 60:40 and 70:30 ratios.Each epimeric set undergoes Dibal-H-mediated detosylation to provide diastereomeric compounds 15-19 in high yields.
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