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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 4
BKCSDE 12(4)
April 20, 1991 

Formal Synthesis of Isocomene
Hyo Won Lee*, Jae Hyun Lee, Ihl-Young Choi Lee
A stereocontrolled synthesis of (±)-isocomene (1) via selective monoketalization of tricyclo[,5]undeca-4,7-dione(13) was reported. Grignard reaction of bicyclic enone 10, which was prepared from 2-methyl-1,3-cyclopentadione, gave the 1,4-addition product 11. The subsequent aldol condensation product 12 was converted to mesyl derivative 13. Transformation from 13 to the desired product 19 was achieved by a series of reactions, i.e., the selective monoketalization at C-4 carbonyl group, the elimination of a mesyl group, Birch alkylation, methylation at C-6, the reduction of carbonyl group, the dehydration of alcohol 18, and hydrolysis of the ketal group.
392 - 397
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