2001 Fiscal Year Final Research Report Summary
An Application of Electrocyclic Reaction for the Synthesis of Pyridoindole Alkaloids
| Project/Area Number |
11672131
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Fukuyama University |
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Principal Investigator |
HIBINO Satoshi Fukuyama Univrsity., Faculty of Pharmacy and Pharmaceutical Sciences, Professor, 薬学部, 教授 (60112885)
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| Project Period (FY) |
1999 – 2001
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| Keywords | (R)-(-)-pyridindolol K1 / (R)-(-)-pyridindolol K2 / (R)-(-)-pyridindolol / mecesengricin / (R)-(+)-oxopropaline D / electrocyclic reaction / synthesis / absolute congifuration |
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| Research Abstract |
1.The first enantioselective total synthesis of (R)-(-)-pyridindolol K2 together with its enantiomer was established in a nine-step or ten step sequence based on the construction of β-carboline N-oxide through the thermal electrocyclic reaction of a 1-azahexatriene system involving the indole 2, 3-bond or the thermal cyclization of 3-ethynylindole-2-carbaldehyde oxime, followed by the Sharpless asymmetric 1, 2-dihydroxylation. In addition, the asymmetric total syntheses of (R)-(-)-pyridindolol K1 and (R)-(-)-pyridindolol were also completed using the same starting material.
2.A total synthesis of α-carboline alkaloid, mescengricin has been investigated by the construction of α-carboline framework based on the thermal electrocyclic reaction of 2-azahexatriene system involving the indole 2, 3-bond. The construction of the glycerolester and the δ-lactone part at the 4-and 2-positions of α-carboline nucleus were established using 7-demethoxy-α-carboline, respectively. We are now investigation of a total synthesis of mecsengricin using 7-methoxy-α-carboline framework.
3.The absolute configuration of (+)-oxopropaline D was determined as R-configuration by the asymmetric synthesis of (R)-(+)-oxopropaline D acetonide.
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