1992 Fiscal Year Final Research Report Summary
Efficient Synthesis of Sulfur-functionalized Cycloalkanol as a Chiral Synthon.
| Project/Area Number |
03453027
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | Mie University |
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Principal Investigator |
FUJISAWA Tamotsu Mie University,(Department of Chemistry for Materials)Faculty of Engineering, 工学部, 教授 (60115730)
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| Project Period (FY) |
1991 – 1992
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| Keywords | Bakers' Yeast Reduction / Sulfur-containing Chiral Synthon / Stereoselective Reduction / Prostaglandin Intermediate / Aggregation Pheromone / Chiral Cycloalkanol / Tetrahydrothiopyran / Ranberg-Baecklund Reaction |
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| Research Abstract |
The stereoselective reduction of sulfur-functionalized cyclic ketones with bakers' yeast leading to cyclic carbinols bearing two adjacent chiral centers and the subsequent transformations into biologically interesting compounds were studied. The bakers' yeast reduction of 2-phenylthiocyclopentanone, 2-phenylthiocyclohexanone, and 2-phenylthio-2-cyclopentenones proceeds well to give optically pure (1S,2R)-1-phenylthio-cycloalkanols. Furthermore, 4-oxo-3-tetrahydrothiopyranylacetates were reduced with bakers' yeast to give optically pure (3S,4S)-4-hydroxy-3-tetrahydrothiopyranylacetate, which was converted into an optically pure prostaglandin intermediate. The bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones gave (3S,4S)-3-acyl-4-hydroxytetrahydro-thiopyrane with high regio-and enantioselectivity. In particular, the reduction of 3-propionyltetrahydrothiopyran-4- one took place regioselectively to give a single (3R,4S)-isomer in optically pure form in good yield, and the subsequent desulfurization by Raney-Ni gave the insect aggregation pheromone, (-)-(4R,5S)-Sitophilure with high optical purity.
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