Synthetic Studies on Antineoplastic Marine Prostanoids.

抗肿瘤海洋前列腺素的合成研究。

• 批准号: 60571004
• 负责人: YAMADA Yasuji
• 金额: $ 1.09万
• 依托单位: Tokyo College of Pharmacy
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1985
• 资助国家: 日本
• 起止时间: 1985 至 1986
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-60571004/
• 关键词: punaglandin; prostanoid; antineoplastic compound; total synthesis; 天然物構造式訂正

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.

Scheuer等人报道了从夏威夷海珊瑚Telesto riisei中分离的氯化前列腺素类punaglandins（PUG）的结构。PUG 3和4分别假定为式2和式1，其具有强的抗肿瘤活性。本研究对PUG 3和PUG 4的合成进行了研究，首先通过手性环戊烯酮（-）-3与<alpha>2-脱氧-D-核糖的手性侧链4连接得到化合物1。然而，合成的1（5S，6S，12 S）与PUG 4不相同。因此，所有可能的非对映异构体：6（5S，6 R，12 S）; 7（5S，6S，12 R）; 9（5S，6 R，12 R）通过类似的合成技术合成。结果，发现化合物7与PUG 4的天然真实样品相同。对PUG 3的合成研究表明，PUG 3的聚集态结构为8。完成了PUG 3和PUG 4的全合成，并对其结构进行了修正。

项目成果

Hiroto Nagaoka: "Synthesis of Punaglandin 3 and 4. Revision of the Structures" Journal of the American Chemical Society. 108. 5019-5021 (1986)

Hiroto Nagaoka：“Punaglandin 3 和 4 的合成。结构的修订”美国化学会杂志。

Hiroto Nagaoka: Journal of the American Chemical Society. 108. 5019-5021 (1986)

长冈博人：美国化学会杂志。