Tetrahedron p. 6607 - 6622 (1988)
Update date:2022-07-29
Topics:
Tokoroyama, Takashi
Fujimori, Kaoru
Shimizu, Takayoshi
Yamagiwa, Yoshiro
Monden, Mitsugu
Iio, Hideo
A general method for the syntheses of cis- and trans-clerodane diterpenoids has been developed and its applications to the total syntheses of both representatives 11 and maingayic acid (32) in racemic forms are described.The common Δ4-3-octalone intermediates 2a and 2b were prepared from 3,4-dimethyl-2-cyclohexenone by a stereospecific conjugate addition-alkylation sequence and the subsequent thermodynamically controlled annelation.The dimethylcuprate addition to 2a followed by enolate trapping afforded stereospecifically the cis-alcohol 12, from which (+/-)-11 has been synthesized.On the other hand hydrocyanation of 2b gave trans-intermediate 33, and then it has been converted to (+/-)-maingayic acid (32).
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(1987)
