77(P63) 海産プロスタノイドpreclavulone Lactoneの構造と合成(ポスター発表の部)

概要

論文の詳細を見る
Two new marine prostanoids, preclavulone lactone I (1) [C_<20>H_<28>O_3, [α]_D-168.0°(CHCl_3)] and II (2) [C_<20>H_<28>O_3, [α]_D-110.0°(CHCl_3)], were isolated from the Okinawan soft coral, Clavularia viridis. Their plane structures were elucidated based on spectroscopic analysis involving two-dimensional NMR spectra (^1H-1^H COSY, ^<13>C-^1H COSY, HMBC). The stereostructure of 1 was determined from the results of the total synthesis. The synthesis was performed starting from (S)-(-)-malic acid via a key intermediate 8, which possesses a trans configuration of the iodomethyl group and ω side chain. (4S, 8R, 12S)-1 was synthesized by the reaction of 8 with acetylenic compound 14 having an S-configration followed by modification of the functional groups. (4R, 8R, 12S)-1 was also synthesized similarly. The spectral data of the synthetic (4S, 8R, 12S)-1 were identical with those of natural preclavulone lactone I (1), but the sign of the optical rotation of the synthetic compound was shown to be different from that of natural 1, demonstrating the absolute stereochemistry of (4R, 8S, 12R) for 1. Preclavulone lactone I (1) is regarded as an important intermediate in the biosynthesis from preclavulone A (5) to clavulones.
天然有機化合物討論会の論文
1996-09-02