73 セコタキサン骨格および二,三のセンブレン型天然物の合成

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Having achieved the biogenetic type synthesis of cembrenoids starting from chloro ketone (2), easily prepared from 1, we have further continued the synthetic efforts on the construction method of the secotaxane skeleton (3), which is biogenetically related with cembrenoid. We have also accomplished the synthesis of several kinds of naturally occurring cembrenoids. These results are discussed in this symposium. I. Synthesis of Secotaxane skeleton Our synthetic strategy of secotaxane skeleton is based on the slight modification of the biogenetic scheme in such a way that C_8-C_9 bond of III is connected after construction of A ring by C-C bond formation between isopropyl cation and C_<10>-position of an intermediate (II)(C_8-C_9 is not bonded). The seco-cembrene (II) is prepared by head to tail coupling reaction of two geranyl units, both of which are properly functionalized by X and Z groups so as to make the C_8-C_9 bonding at the final stage. Based on this plan, we have succeeded in the synthesis of neocembrene (8) and secotaxane skeleton (3) as illustrated in the schemes. II. Synthesis of several kinds of cembrenoids The naturally occurring cembrenoids, 2-hydroxy- (15) and 1,14-dehydro-6,7-oxidonephthenols (17), and cembrenol (23) were prepared from chloro ketone (2) as indicated in the synthetic schemes. The present synthesis supports unequivocally the assigned structures of these oxygenated cembrenoids.
天然有機化合物討論会の論文
1978-08-22

73 セコタキサン骨格および二,三のセンブレン型天然物の合成

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