[The use of microbial and enzymatic function in organic synthesis. Total synthesis of the aglycone of venturicidins A and B].
The synthesis of chiral synthons by means of microbial and enzymatic function and its application to the synthesis of complex, bioactive substances, the aglycone of venturicidins A and B are reviewed. 1) The syntheses of chiral synthons having two chiral centers are described based on the microbial asymmetric reduction of alpha-methyl beta-keto esters or enzymatic asymmetric hydrolysis of alpha-methyl beta-acetoxy esters. 2) The new chiral synthons synthesized in 1) have been successfully applied for the total syntheses of oudemansins A and B. 3) Purification and properties of the asymmetric reduction enzyme of alpha-methyl beta-keto esters in Saccharomyces cerevisiae or Saccharomyces fermentati were investigated. 4) Formal total synthesis of (-)-indolmycin is described based on the asymmetric hydrolysis of alpha-acetoxy ester with lipases. 5) Enzymatic hydrolysis in organic solvents for kinetic resolution of water-insoluble alpha-acyloxy esters with immobilized lipases is described. 6) The first total synthesis of the aglycone of venturicidins A and B has been successfully achieved from the new chiral synthon based on the developed method in 1).
Akita
H
H
RIKEN Institute, Saitama, Japan.
D004952:Esters; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D012997:Solvents; D014698:Venturicidins / Q000138:chemical synthesis*
D004952:Esters; D012997:Solvents; D014698:Venturicidins; C068161:venturicidin A; C068160:venturicidin B; D008049:Lipase