发明授权
- 专利标题: Dl-strigol intermediate
- 专利标题(中): Dl-strigol中间体
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申请号: US532759申请日: 1974-12-13
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公开(公告)号: US3972916A公开(公告)日: 1976-08-03
- 发明人: Charles J. Sih
- 申请人: Charles J. Sih
- 申请人地址: WI Madison
- 专利权人: Wisconsin Alumni Research Foundation
- 当前专利权人: Wisconsin Alumni Research Foundation
- 当前专利权人地址: WI Madison
- 主分类号: C07D307/93
- IPC分类号: C07D307/93 ; C07C61/38
摘要:
A process for preparing dl-strigol, a potent seed germination agent, which comprises preparing the 2-bromomethyl-substituted methyl ester of 2,6,6-trimethylcyclohex-1-en-3-one-1-carboxylic acid, alkylating and cyclizing the said compound with an excess of dimethyl sodiomalonate to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-carboxylate and its enol, subjecting the said keto and enol forms of the compound, in admixture, to alkylation with methyl bromoacetate followed by acidic hydrolysis and spontaneous decarboxylation to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid, reducing the said acetic with a hydride reducing agent and recovering and separating the resulting 1,4-cis and trans-dihydroxy-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid lactones, formylating each of the cis and trans .gamma. lactones, alkylating the respective resulting hydroxy methylene lactones with bromobutenolide and recovering dl-strigol, dl-4'-epi-strigol, dl-4-epi-strigol and dl-4,4'-diepi-strigol.New compounds useful as intermediates in the above process are also shown.