1994 Fiscal Year Final Research Report Summary
Synthesis and molecular desighn of biological active aromadendrane type of sesquiterpenes
| Project/Area Number |
04671285
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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 | Okayama University |
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Principal Investigator |
HARAYAMA Takashi Okayama Univ.Prof.Fac.Pharm.Sci., 薬学部, 教授 (30025712)
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| Project Period (FY) |
1992 – 1994
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| Keywords | aromadendrane / sesquiterpene / bicyclo [5.1.0] octane / higher order orqanocuprate / dibromocyclopropane / differential substitution reaction / ミブロモシクロプロパン |
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| Research Abstract |
1.Improved synthesis of 2-carbomethoxycyclohept-2-en-1-on
It was clearly found that a high dilution method was not necessary for synthesis of the title compound as reported previously.
2.Synthesis of 8,8-dimethylbicyclo [5.1.0] octanes from 8,8-dibromobicyclo [5.1.0] octanes Higher order organocuprate Prepared from commercially avialable methyl lithium and cuprous cyanide was very effective for the synthesis of title compound.
3.One-pot unsymmetrical double substitution of 8,8-dibromobicyclo [5.1.0] octane and its stereochemistry
A differential substitution reaction of dibromocyclopropane in one-pot using higher order organocuprate-allyl bromide gave a desired product in a moderate chemical yield and stereo-selectivity. Its stereochemistry was deduced by the reaction mechanism and by chemical means.
4.Synthesis 8,8-dimethylbicyclo [5.1.0] octenone
Reaction of 8,8-dimethylbicyclo [5.1.0] octanone with phenylselenyl chloride followed by oxidation with hydrogene peroxide gave octenone derivative in a good yield.
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