- Cyclopentanoids from Phenol. VI Chiral Prostanoid Intermediates
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(4S)-4-(t-Butyldimethylsilyloxy)-3-chlorocyclopent-2-enone (3a) is prepared from phenol in five steps including resolution of the initial ring-contraction product, (1RS,4RS)-3,5,5-trichloro-1,4-dihydroxycyclopent-2-ene-1-carboxylic acid .Conjugate addition-elimination reactions of functionalized alylmagnesiocuprate reagents with the synthon (3a) lead to 3-substituted (4S)-4-hydroxycyclopent-2-enone derivatives, and thence by stereospecific transposition of the ring oxygen functions to 2-substituted (4R)-4-hydroxycyclopent-2-nones.The efficiency and versatility of the route are demonstrated by synthesis of the (4R)-2-(6-methoxycarbonylhexyl)- and (4R)-2-(7-hydroxyheptyl)-4-hydroxycyclopent-2-enone derivatives, (5b) and (6b) respectively, which are important intermediates in prostaglandin and prostanoid synthesis.
- Gill, Melvyn,Rickards, Rodney W.
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p. 1063 - 1071
(2007/10/02)
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- Cyclobutyl substituted derivatives of prostaglandin analogs
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Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.
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- Process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone
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Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula STR1 wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in t
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