| Project/Area Number |
60570975
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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 | TOHOKU UNIVERSITY |
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Principal Investigator |
OGASAWARA Kunio Tohoku University, Assoc. Professor, 薬学部, 助教授 (60004602)
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| Co-Investigator(Kenkyū-buntansha) |
TAKAHASHI Michiyasu Tohoku University, Technical Official of Ministry of Educati, 薬学部, 教務職員 (80089789)
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| Project Period (FY) |
1985 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1986: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1985: ¥1,200,000 (Direct Cost: ¥1,200,000)
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| Keywords | Diels-Alder Reaction with Reverse Electron Demand / Hetero-Diels-Alder-Reaction / Intramolecular Diels-Alder Reaction / Chiral Synthesis / セコイリドイドモノテルペン / ヘテロヨヒンビンアルカロイド / 分子内ヘテロ・ディールス・アルダー反応 |
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| Research Abstract |
Enantioselective reaction employing intramolecular hetero-Diels-Alder reaction with reverse electron demand has been examined. Reaction of the two isomeric glyceraldehydes, (2) and (3), prepared from diethyl L-tartrate (1), with Meldrum's acid underwent smooth concurrent condensation and intramolecular Diels-Alder reaction with reverse electron demand to give the corresponding cycloadducts in highly diastereoselective manners. It was found that the E-dienophile (2) afforded the cis-5/6-adduct (4) and the Z-dienophile (3) afforded the trans-5/6-adduct (5) each as a single epimer. Using two adducts a formal route to all possible stereoisomers of the heteroyohimbine alkaloids has been established. Furthermore, a new route to the secoiridoid monoterpene, (-)-methyl elenolate(6), and both cis- and trans-D/E ring heteroyohimbine alkaloids, (-)-tetrahydro-alstonine (7) and (-)-ajmalicine (8), has been developed using the cis-5/6-adduct (4) as a single precursor.
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