Synthetic Studies on Antineoplastic Marine Prostanoids.

Scheuer等报道了从夏威夷八珊瑚中分离到的氯化前列腺素（PUGs）的结构。公式2和1分别假设PUG 3和4具有较强的抗肿瘤活性。本研究对PUG 3和PUG 4的合成进行了研究。首先，将手性环戊酮(-)-3与2-脱氧-d核糖衍生的手性< α > -侧链4连接，合成化合物1。但合成1 （5S、6S、12S）与PUG 4不完全相同。因此，所有可能的非对映体：6 (5S,6R,12S)；7 (5 s 6 s 12 r);9 （5S,6R,12R）采用类似合成技术合成。结果发现，化合物7与PUG 4的天然真实标本相同。同样，对PUG 3的合成研究显示其集束结构为8。本文完成了pug3和pug4的全合成，并对其进行了结构修改。

The structures of chlorinated prostanoids punaglandins (PUGs) isolated from Hawaiian octocoral Telesto riisei have been reported by Scheuer et al. Formula 2 and 1 were postulated for PUG 3 and 4, respectively, which have potent antineoplastic activity. In this research, the synthesis of PUG 3 and 4 has been studied.Firstly, compound 1 was synthesized by linking of the chiral cyclopentenone (-)-3 to the chiral <alpha> -side chain 4 derived from 2-deoxy-D-ribose. However, the synthetic 1 (5S,6S,12S) was not identical with PUG 4. Therefore, all possible diastereomers: 6 (5S,6R,12S); 7 (5S,6S,12R); 9 (5S,6R,12R), were synthesized by analogous synthetic technique. As the result, compound 7 was found to be identical with natural authentic specimen of PUG 4. Similary, synthetic study on PUG 3 revealed its collect structure as 8. Here the total synthesis of both of PUG 3 and 4 was accomplished and it made the structural revision.