Total syntheses of (-)-spirooliganones A and B.
The enantioselective syntheses of (-)-spirooliganones A and B have been accomplished in eight steps from commercially available starting materials. Noteworthy transformations include a three-component hetero-Diels-Alder cycloaddition to construct the tetracyclic core of spirooliganones, a Sharpless asymmetric dihydroxylation, and a tandem oxidative dearomatization/cyclization to build the oxa-spiro cyclohexadienone skeleton. The straightforward syntheses were performed without protecting groups.
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, P. R. China.
Lin
L
Wei
Mingxing
M
Xiao
Zhixiang
Z
Xie
D003500:Cyclization; D061565:Cycloaddition Reaction; D029523:Illicium / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D013141:Spiro Compounds; C586354:spirooliganone A