89295-89-6Relevant academic research and scientific papers
A GENERAL METHOD FOR THE SYNTHESIS OF CLERODANE DITERPENOIDS. STEREOSPECIFIC TOTAL SYNTHESES OF (+/-)-15,16-EPOXY-CIS-CLERODA-3,13(16),14-TRIENE AND (+/-)-MAINGAYIC ACID
Tokoroyama, Takashi,Fujimori, Kaoru,Shimizu, Takayoshi,Yamagiwa, Yoshiro,Monden, Mitsugu,Iio, Hideo
, p. 6607 - 6622 (2007/10/02)
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).
A Versatile Method for the Synthesis of Clerodane Diterpenoids: Synthesis of cis and trans Representatives
Tokoroyama, Takashi,Fujimori, Kaoru,Shimizu, Takayoshi,Yamagiwa, Yoshiro,Monden, Mitsugu,Iio, Hideo
, p. 1516 - 1518 (2007/10/02)
Application of stereospecific conjugate addition reactions to Δ4-3-octalone intermediates has led to the total synthesis of both cis- and trans-clerodane diterpenes.
