Abstract
A prostaglandin F 2α precursor containing all structural features from C 6 to C 20 with 8 R, 9 S, 11 R and 12 R chirality is obtained by the one step formation of two C-C bonds in the B 12-catalyzed radical cyclization-addition sequence starting from a chiral cyclopentene bromoacetal and l-octyne-3-one. The B 12-catalyzed radical cyclization-elimination sequence of a chiral cyclopentene precursor leads to (-)-(3a R,6a S)-3,3a,6,6a-tetrahydro-2H-cyclopenta abfuran-2-one. Its (+)-(3a S,6a R-enantiomer is obtained via B 12-catalyzed, enantio- selective isomerization of cyclopentene oxide to (R)-2-cyclopentene-l-ol followed by the B 12-catalyzed radical cyclization-elimination sequence of its bromoacetal.
Published Version
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