78824-82-5Relevant articles and documents
The Three-Component Coupling Synthesis of Prostaglandins
Suzuki, M.,Yanagisawa, A.,Noyori, R.
, p. 4718 - 4726 (2007/10/02)
A convergent one-pot construction of the prostaglandin (PG) framework has been accomplished by the organocopper-mediated conjugate addition of the S configurated ω side-chain unit to a protected (R)-4-hydroxy-2-cyclopentenone followed by trapping of the enolate intermediate by α side-chain alkyl halides.Transmetalation with use of triphenyltin chloride at the enolate stage serves as key operation for the succesful three-component coupling synthesis.The use of methyl (Z)-7-iodo-5-heptenoate as the α side-chain component allows short synthesis of PGE2 and PGD2.Introduction of a triple bond at the C-5-C-6 positions with methyl 7-iodo-5-heptynoate as the α side-chain synthon has opened a general entry of PGs.The protected 5,6-didehydro-PGE2 derivatives are convertible to a variety of PGs of 1 and 2 series by the controlled hydrogenation of the C-5-C-6 unsaturated bonds and α-selective (100percent) reduction of the C-9 keto function, if necessary.Lithium aluminum hydride reagents modified by (R)- and (S)-2,2'-dihydroxy-1,1'-binaphthyl exhibit a unique kinetic discrimination in reduction of PGE type compounds.A protected 5,6-didehydro-PGF2α has been transformed stereoselectively to PGI2 by using intramolecular alkoxypalladation/depalladation as the key step.
A SHORT WAY TO PROSTACYCLIN
Suzuki, M.,Yanagisawa, A.,Noyori, R.
, p. 1187 - 1188 (2007/10/02)
A facile, stereospecific preparation of prostacyclin has been accomplished starting from a 5,6-dehydroprostaglandin F2α derivative.
