Prostaglandin synthesis from a fulvene with the ω-side chain equivalent |
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Authors: | Kunikazu Sakai Takeo Kobori Tamotsu Fujisawa |
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Institution: | Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229, Japan;Chemistry Department of Resources, Mie University, Tsu, Mie 514, Japan |
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Abstract: | The acid-catalyzed hydrolysis of the Diels-Alder adduct of 6-(2,2-ethylene-dioxyheptyl) fulvene with 2-chloroacrylonitrile gave 7-anti-(3-oxo-1-trans-octenyl)-2-chloro-2-cyanobicyclo2.2.1]hept-5-ene, which is an intermediate of 12-epi-prostaglandine. On the other hand, the hydrolysis of 7-(3,3-ethylenedioxyoctylidene)bicyclo-2.2.1]hept-5-en-2-one, obtained from the Diels-Alder adduct of the fulvene with 2-chloroacryloyl chloride, gave a mixture (3:2) of 7-anti- and 7-syn-(3-oxo-1-trans-octenyl)bicyclo2.2.1]hept-5-en-2-one. The latter compound was oonverted into prostaglandin F2α. |
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