OPTICALLY ACTIVE 4-HYDROXY-1-OCTENE COMPOUND AND PRODUCTION THEREOF

摘要

NEW MATERIAL:The optically active compound of formula I [R<1> is H, tri(1-7C hydrocarbon)silyl or group forming acetal bond or ester bond together with O of OH group; * is C atom having induced optical activity]. EXAMPLE:(1E,4S)-1-iodo-4-methyl-4-trimethylsilyloxy-1-octene. USE:A novel omega-chain raw material for the synthesis of 15-deoxy-16-hydroxy-16- methylprostaglandins having optical activity at 16-site and useful as a medicine. PREPARATION:The compound of formula I wherein R<1> is R<11> can be produced by carrying out the hydroboration of an optically active 4-hydroxy-4-methyl-1- octene compound of formula II (R<11> is R<1> except for H) with a reagent such as dialkylborane in a solvent, adding an oxidizing agent to the reaction system without delay and iodizing the product with aqueous alkali and I2. The product can be converted to another compound of formula I wherein R1 is H by removing the protecting group.