松叶蜂性信息素中间体的合成  

Synthesis of the Intermediates of Sex Pheromone of Pine Sawfly

作　　者：孟祎[1] 许艳杰[1] 陈立功[1] 

机构地区：[1]天津大学药物科学与技术学院,天津300072

出　　处：《精细化工》2003年第8期501-505,共5页Fine Chemicals

摘　　要：对类欧松叶蜂(Diprionsimiles)和红头新松叶蜂(Neodiprionlecontei)性信息素前体化合物———(2S,3S,7S) 3,7 二甲基 2 十五碳醇的合成进行了设计和研究,重点对其中的两个中间体(2S,3S) 2 甲基 3 苄氧基丁醛和(S) 3 甲基十一碳 6 烯醇进行了合成。以顺 2 丁烯为原料,经Browncrotylation反应,得到(2S,3S) 3 甲基戊 4 烯 2 醇,该化合物羟基经苄基保护,所得产物于室温下依次进行OsO4氧化、NaIO4氧化,合成了(2S,3S) 2 甲基 3 苄氧基丁醛,总收率为56 3%。(S) 香茅醇经羟基保护、OsO4氧化、NaIO4氧化、Wittig反应、脱保护等反应,于室温条件下合成了(S) 3 甲基十一碳 6 烯醇,总收率为40 0%。为此种松叶蜂性信息素的全合成奠定了基础。Synthesis of the precursor of the sex pheromone of pine sa wfly Diprion similes and Neodiprion lecontei--(2S,3S,7S)-3,7-dimethy l-2-pentadecanol was designed and examined. The syntheses of the related two i ntermediates were emphatically studied.(2S,3S)-2-methyl-3-benzoxybutyral dehyde was obtained from cis-2-butene through Brown crotylation reaction,p rotection of hydroxyl with benzyl,oxidation at room temperature with OsO4 and then with NaIO4 in overall yield of 563%.(S)-3-methylundec-6-enol wa s prepared from (S)-citronellol through hydroxyl protection,OsO4 oxidatio n,NaIO4 oxidation,Wittig reaction and de-protection at room temperature in ov erall yield of 400%.These results are the basis of total synthesis of sex pher omone of this kind of pine sawfly.

关 键 词：松叶蜂 性信息素 3 7-二甲基-2-十五碳醇 2-甲基-3-苄氧基丁醛 3-甲基十一碳-6-烯醇 

分 类 号：O623.4[理学—有机化学]