期刊
ORGANIC LETTERS
卷 11, 期 14, 页码 3104-3107出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol901213d
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资金
- MICINN [CTQ2008-000763]
- IRB Barcelona
A new approach to the synthesis of prostaglandin and phytoprostanes B-1 is described. The key step is an intermolecular Pauson-Khand reaction between a silyl-protected propargyl acetylene and ethylene. This reaction, promoted by NMO in the presence of 4 angstrom molecular sieves, afforded the 3-tert-butyldimethylsilyloxymethyl-2-substituted-cyclopent-2-en-1-ones (III) in good yield and with complete regioselectivity. Deprotection of the silyl ether, followed by Swern oxidation, gave 3-formyl-2-substituted-cyclopent-2-en-1-ones (II). Julia olefination of the aldehydes II with the suitable chiral sulfone enabled preparation of PPB1 type I and PGB(1).
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