23 Abietic Acidより2,3の天然物の合成研究

概要

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The synthesis of some natural products has been achieved from 1-abietic acid (1), a major component of pine rosin. I) Synthesis of A-Ring Substituted Natural Diterpene 1β-Bromo ester (15), a key intermediate in the synthesis of A-ring substituted diterpenes, was obtained by an interesting bromination (NBS, Ac_2O-c.H_2SO_4) of phenacylidene ester (14) derived from 1-abietic acid (1). Salviol (2), isolated from Salvia miltiorrhiza, and 2β-acetoxysugiyl methyl ether (3), isolated from Podocarpus ferrugineus, were synthesized from 1β-bromo ester (15) by several steps. II) Synthesis of Gibberellin A_<12> A/B-trans-Hydrofluorene compound (41), obtained via a benzilic acid rearaangement of dioxo ester (35) derived from 1-abietic acid (1), was converted by 8 steps into 13β-carboxy diester (84). Intramolecular carbene insertion of diazoketone (86) gave 5-membered ring ketone (87). After partial hydrolysis, half acid (88) was methylated to give diester (89), which was identical with GA_<12> nor-ketone dimethyl ester synthesized from natural GA_<12> (4). The conversion of half acid (88) into [^<14>C]gibberellin A_<12> had been accomplished by B.E. Cross, et al.
天然有機化合物討論会の論文
1975-10-01