1993 Fiscal Year Final Research Report Summary
Synthetic Study on Antitumor Antivacterial Marine Alkaloid Manzamine A
| Project/Area Number |
04671283
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Chiba University |
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Principal Investigator |
TORISAWA Yasuhiro Chiba University, Faculty of Pharmaceutical Sciences, research associate, 薬学部, 助手 (80119601)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAGAWA Masako Chiba University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 助教授 (40009171)
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| Project Period (FY) |
1992 – 1993
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| Keywords | manzamine A / dihydropyridiones / Diels-Alder reaction / pyrroloisoquinoline / azocin lactam / Wittig reaction / PFP ester |
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| Research Abstract |
For the challenging construction of the complex azacyclic core structure of manzamine A, we have been investigating a viability of the Diels-Alder reaction of 3-alkyldihydropyridinones. Thus, after various attempts on the search for a suitable dienophile partner as well as on the practical reaction conditions, we have found the high-pressure D-A reaction of 1 with Danishefsky diene, which furnished the tricyclec core structrue (2) of manzamine A.After this initial success, we have developed another moer practical and efficient D-A reaction of the two new dienophiles (3), which have NCOCF_3 group at the side chain. With this dienophiles, D-A reaction proceeded under normal pressure to afford the enone (4). Utilizing this key reaction, the new tricyclic ley intermediate (5) was prepared, which was efficiently converted to the alchohol (6). Oxidation of 6 followed by the Witting reaction allorded the acid (7) which was then purified by the PFP ester (8). Careful deprotection and base treatment of 8 furmished the tetracyclic core (9) of manzamine A.
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