103(P28) 神経樹状突起伸長作用を有するエポラクタエンの全合成(ポスター発表の部)
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概要
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Epolactaene, which was isolated from fugal strain. Penicillium sp. BM1689-P by Osada et al., possesses a potent neurite outgrowth activity in a human neuroblastoma cell line SH- SY5Y. The characteristic features of this compound are the α,β-epoxy-γ-lactam core and a conjugated triene moiety in the side chain. Herein we describe a highly convergent total synthesis of epolactaene. The key step is the F^--catalyzed coupling reaction of α-trimethylsilyl derivative of β-angelica lactone epoxide and the side-chain aldehyde. Total synthesis of epolactaene was accomplished as follows. 1) The vinyl iodide 4 was prepared starting from 1,4-butanediol using stereoselective carbometallation of Cp_2TiCl_2-Me_3Al to the enyne. 2) Vinylstannane 5, other substrate for the Stille coupling was prepared by three steps from the known stannylalcohol 13. 3) Construction of the conjugated triene moiety 16 was achieved by the Pd(CH_3CN)_2Cl_2-catalyzed Stille coupling in the presence of Cu(I) in high yield. After deprotection of MPM group by HCl, followed by Swern oxidation, resulting aldehyde was subjected to the Wittig reaction to obtain the side chain aldehyde 3. 4) After a number of examinations on the reaction of α,β-epoxylactone and aldehyde, we found that aldol-type product was obatained by two step procedure. Thus, epoxylactone was initially converted into the α-trimethylsilyl derivative and the latter was reacted with aldehyde in the presence of n-Bu_4NF affording the condensation product in good yield. This methodology was successfully applied to the enantiomerically pure β-angelica lactone epoxide prepared from L-xylose and the side chain aldehyde 3 to obtain 22 in good yield. 5) Transformation of 22 to epolactaene was accomplished by three step. Structure of synthetic epolactaene was confirmed by the comparison of ^1H-, ^<13>C-NMR and [α]_D value with those of natural epolactaene.
- 天然有機化合物討論会の論文
- 1998-08-31
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