
TY  - JOUR
A1  - Haynes, RK 
A1  - Lambert, DE 
A1  - Schober, PA 
A1  - Turner, SG 
T1  - An Extremely Simple Route to a Prostaglandin Precursor: Hexamethylphosphoric-Triamide-Mediated Conjugate Addition of 1-(Phenylthio)Oct-2-Enyllithium to 4-Tert-Butoxycyclopent-2-Enone and Triphenyltin-Chloride-Assisted Reaction of the Enolate With Methyl 7-Iodohept-5-Ynoate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1987
VL  - 40
IS  - 7
SP  - 1211
EP  - 1222
KW  - 
UR  - https://doi.org/10.1071/CH9871211 
N2  - Reaction of 4-t-butoxycyclopent-2-enone with (E)-1-(pheny1thio)oct-2-enyllithium in tetrahydrofuran containing 1.5 equivalents of hexamethylphosphoric triamide at - 78º followed by treatment of the resulting enolate with one equivalent of triphenyltin chloride and then with methyl 7-iodohept-5-ynoate at - 20º gives the vicinally dialkylated cyclopentanone, methyl (a-9-oxo-1l-t-butoxy-13-(phenylthio)prost-14-en-5-ynoate, as a 1 : 1 mixture of diastereomers epimeric at C13, in 70-72% overall yields from the octenyllithium reagent. Stereoselective reduction of the C9 carbonyl, conversion of the sulfide into the allylically transposed alcohol, and removal of the t-butyl group by means of iron(III) chloride in acetic anhydride at 0º provides a triacetate which is converted into racemic methyl 5,6-didehydroprostaglandin F2a methyl ester as a 1 : 1 mixture of diastereomers epimeric at C15. 
ER  -

