PURPOSE: To produce an optically active compound useful as an intermediate for synthesis of vitamin D3 derivatives in a high yield without requirement of optical resolution by reacting lithium trisilylacetylide with an epoxide in the presence of a Lewis acid.
CONSTITUTION: This compound of formula II is produced by reacting lithium (1 to 7C hydrocarbon)silylacetylide with a compound of formula I [R1 is H, a tria(1 to 7C hydrocarbon)silyl, etc.] in the presence of a Lewis acid (preferably boron trifluoride ether complex) generally at ≤-70°C for 1min to 3hr. Specifically, trimethylsilylacetylene is reacted with n-butyl lithium to obtain lithium trimethylsilylacetylide and the resultant compound is then reacted with 3-(tert- butyldiphenyloxy)-5,6-epoxy-1-hexene which is a compound of formula I to synthesize 3-(tert-butyldiphenylsilyl-oxy)-5-hydroxy-8-trimethylsilyl-1-octen-7-yne.
TANABE MASAYASU
MANABE KENJI
HASATO ATSUO
