Enantioselective constructions of quaternary carbons and their application to the asymmetric total syntheses of fredericamycin A and discorhabdin A

Kita, Yasuyuki; Fujioka, Hiromichi

doi:10.1351/pac200779040701

Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 701-713

http://dx.doi.org/10.1351/pac200779040701

Enantioselective constructions of quaternary carbons and their application to the asymmetric total syntheses of fredericamycin A and discorhabdin A

Yasuyuki Kita and Hiromichi Fujioka

Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565, Japan

Abstract: An efficient enantioselective construction of quaternary carbons including spiro carbons is an area of intense interest due to the importance of these units as components of biologically active natural products. Prominent methods are presented for the synthesis of chiral, nonracemic quaternary carbon centers by (i) stereospecific rearrangement of optically active epoxides, (ii) enzyme-catalyzed resolution, and (iii) hypervalent iodine reagent-induced ipso-substitution of para-substituted phenol derivatives. These methods were applied to the total syntheses of fredericamycin A and discorhabdin A.