【摘要】 本文报道的一条合成路线是以(+)-甘油醛缩丙酮(2)为原料,各经过9～10步反应可分别合成午毒蛾光学活性性信息素1a及其三个光学异构体1b～d,总得率达20～30％。更多还原

【Abstract】 The title compounds 1a～d were synthesized from（+）-（R）-glyceraldehyde acetonide （2） obtained from mannitol in 9～10 steps in an overall yield of 20～30%. Thus, Grignard reaction of 2 with n-C₁₀H₂₁MgBr yielded a mixture of two diastereoisomers which afforded 3（erythro form, R, S） and 4 （threo form, R, R） by SiO₂ gel chromatography. The free alcohol 3 was reacted with benzyl chloride followed by acidic hydrolysis to give diol 6 which on selective tosylation followed by treatment with 0.25 M methanolic KOH gave an epoxide 8. 8 was treated with（i-hex）₂ OuLi in ether to give 9 which on removal of the benzyl protecting group followed by reaction with HBr-HOAc gave a mixture of 11a and 11b. Finally, treatment of the mixture of 11a and 11b with 0.5M methanolic KOH gave （+）-disparlure（1a）. 1c and 1d were obtained from 9 by the reaction sequences as shown in the Chinese Text. The （-）-disparlure （1b） was obtained from 4 by the reaction sequences of 5’→6’→7’→8’→9’→1b.更多还原