Tetrahedron p. 173 - 182 (1991)
Update date:2022-08-03
Topics: Synthesis Asymmetric synthesis Chiral Catalyst Enantioselective Stereoselective Diastereoselective Reaction
Chen, Bang-Chi
Weismiller, Michael C.
Davis, Franklin A.
Boschelli, Diane
Empfield, James R.
Smith, Amos B.
An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (1) has been achieved.The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester 2 with the new, enatiomerically pure N-sulfonyloxaziridine 7b, affording 1 in 68.5percent ee (60percent yield).Possible transition state structures for the asymmetric oxidation are evaluated.
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