Synthesis of (-)-calicoferol B.
The first total synthesis of (-)-calicoferol B (III) is described. The cyclozirconation product I, prepared in enantiomerically pure form, was converted into the CD ring chiron II. This was coupled with the aromatic A-ring, and then the side chain was constructed with control of relative and absolute configuration to complete the total synthesis of III. The first total synthesis of (-)-calicoferol B (1) is described. The cyclozirconation product 8, prepared in enantiomerically pure form, was converted into the CD ring chiron 6. This was coupled with the aromatic A-ring, and then the side chain was constructed with control of relative and absolute configuration to complete the total synthesis of 1.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Jiang
Qin
Q
Chen
Bei
B
Zhang
Wei
W
Campbell
Carlton L
CL
D000447:Aldehydes; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012632:Secosteroids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D012632:Secosteroids; C469858:calicoferol B