PRODUCTION OF S-OR R-PHOSPHONOTHRIXIN OR ITS ANALOG, AND SYNTHETIC INTERMEDIATE THEREOF

摘要

PROBLEM TO BE SOLVED: To chemically synthesize the subject compound that is an optional enantiomer having biological activities such as plant growth regulating or herbicidal activities different from those of the other by carrying out the asymmetric epoxidation, phosphonation and oxidative decomposition of a dienyl alcohol. SOLUTION: A dienyl alcohol represented by formula I (R<1> is a 1-5C alkyl, phenyl, etc.; R<2> and R<3> are each independently H, a 1-5C alkyl or a 1-5C alkoxyl) is reacted with a D-tartaric acid diester to provide an S-oxirane compound represented by formula II, which is then phosphonated with a salt of a phosphite compound with a metal (halide) to afford a compound represented by formula III (R<4> is a 1-4C alkyl, etc.). The resultant compound is then oxidatively decomposed to provide a compound represented by formula IV. The protecting groups are eliminated to thereby afford S-phosphonothrixin represented by formula V. When the asymmetric epoxidation of the dienyl alcohol represented by formula I is carried out with an L-tartaric acid diester to afford R-phosphonothrixin as the final product.