1986 Fiscal Year Final Research Report Summary

Synthetic Studies on Antineoplastic Marine Prostanoids.

Research Project

Project/Area Number	60571004
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	Chemical pharmacy
Research Institution	Tokyo College of Pharmacy
Principal Investigator	YAMADA Yasuji Tokyo College of Pharmacy, Department of Pharmacology, Professor., 薬学部, 教授 (10057317)
Project Period (FY)	1985 – 1986
Keywords	punaglandin / prostanoid / antineoplastic compound / total synthesis / 天然物構造式訂正
Research Abstract	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.