Mineo Fukui

Meta functionalization of anilines and phenol

Abstract Regioselective introduction of various functional groups on the meta-position of anilines and phenol was achieved by proton abstraction from the chromium tricarbonyl complexes 3 , 5 , 7 with n -BuLi, followed by the addition of electrophiles and decomplexation.

A formal total synthesis of erythromycin A. 1. Facile and stereoselective syntheses of erythronolide a segments based on acyclic stereocontrol

Abstract Two segments, corresponding to the C 1 –C 7 and C 8 –C 15 parts of erythronolide A, were synthesized stereoselectively from the optically active syn -α-methyl-β-hydroxy imides prepared by Zn(BH 4 ) 2 reduction of the corresponding β-keto imides.

Stereoselective synthesis of the functionalized syn-1,3,5,7-tetraol

The syn-1,3,5,7-tetraol derivative 21 was synthesized with complete stereo-selection based on the stereoselective reduction of a six-membered β-keto hemiacetal and a subsequent hemiacetal ring opening.

Stereoselective synthesis of (±)-blastmycinome and formal total synthesis of antimycin A3

(±)-Blastmycinone (2) and the key intermediate 20 for the total synthesis of antimycin A3 (1) have been synthesized based on the stereoselective reduction of β-keto ester and α-hydroxy ketone by means of Zn(BH4)2.

A formal total synthesis of erythromycin A. 2. A convergent synthesis of Woodward's carbamate intermediate

Abstract The key intermediate 1 in Woodwards total synthesis of erythromycin A was synthesized via coupling of the C 1 –C 7 and C 8 –C 15 segments.

Stereoselective acyclic ketone reduction: Synthesis of the synthons having three consecutive chiral centers

Abstract Four possible diastereomers of a functionalized 1,3-dimethyl-2-hydroxy unit were synthesized based on the stereoselective reduction of various acyclic ketones (i.e. reduction of β-keto ester, β-hydroxy ketone, α-hydroxy ketone, and α-silyloxy ketone) and the regioselective ring opening of epoxide by 1,3-dithiane anion.

Stereoselective synthesis of the synthons having three consective chiral centers

Abstract Four possible diastereomers having three consective chiral centers, R-CHMe-CHOH-CHMe-R′, have been synthesized stereoselectively based on the stereoselective reduction of acyclic ketones.