6种松毛虫性信息素前体化合物全合成研究进展

doi:10.11707/j.1001-7488.20200419

Abstract

Abstract:

There are six species of pine caterpillars in China,including pine caterpillars include Dendrolimus punctatus,D. superans,D. tabulaeformis,D. houi,D. spectabilis and D. kikuchii,and all the insects are serious pests of pine forests in China. Pine caterpillars have a strong reproductive capacity. When the pests break out,the all leaves of pines are eaten up quickly,which seriously hinders the growth of trees and even causes the trees to die. Furthermore,the pine caterpillars'infestation cause pines to decline,which can lead to the invasion of stem borers. Therefore,the control of pine caterpillars has always been an important research direction of forest entomologists in China. It is an important part of the comprehensive management of pine caterpillars to find an effective population monitoring method. Sex pheromone is an important means for the comprehensive management of pine caterpillars for its strong specificity and convenient application. Sex pheromone attractants can be used not only to monitor the occurrence period and population dynamics of pine caterpillars,but also to control the population number and prevalence by interfering with their mating. The active ingredients of sex pheromones in the 6 species of pine caterpillars could be divided into two main categories. The derivative of (Z,E)-5,7-dodecadien-1-ol and the derivative of (E,Z)-5,7-dodecadien-1-ol. Their precursors are the corresponding alcohols. In this paper,the synthesis methods of these two precursor compounds were summarized. The total synthesis of (Z,E)-5,7-dodecadien-1-ol could be roughly classified into three different synthetic ways. Route one,the Wittig reaction between aldehydes and phosphoranes; Route two,coupling reaction of E type iodinated alkene with unsaturated hydrocarbons; Other paths of reactions,including anti-Markovnikov addition of substituted olefins; rearrangement of thexylalkenyllalkynylboranes,and coupling reactions of organometallic reagents. In contrast,(E,Z)-5,7-dodecadien-1-ol could be synthesized by two ways. Route one,the Wittig reaction between α,β-unsaturated aldehydes and phosphoranes; Route two,coupling reaction of E type iodinated enol with alkynes. At present,the demand for sex pheromone of pine caterpillars is increasing day by day,and the design and optimization of its synthesis methods have become an important task. Consequently,this review will provide important reference for the researchers who carry out the similar research in China.

Key words: Dendrolimus spp., sex pheromone, (Z, E)-5, 7-dodecadien-1-ol, (E, Z)-5, 7-dodecadien-1-ol, total synthesis

CLC Number:

S763.3

Fu Liu,Zhongwei Yuan,Xiangbo Kong,Sufang Zhang,Zhen Zhang,Zhifeng Guo,Zhenlin Li,Yanhui Song,Yibin Zhou. Research Progress on Total Synthesis of Precursor Components of Sex Pheromones from Six of Pine Caterpillar Species in China[J]. Scientia Silvae Sinicae, 2020, 56(4): 170-180.

Figures/Tables 11

Table 1

The synthesis route of (Z, E)-5, 7-dodecadien-1-ol"

原料 Start materials	合成步骤 Steps	总产率 Overall yield(%)	构型 Configuration	文献 References
2-庚炔-1-醇2-Heptyn-1-ol	6	—	Z5, E7;E5, E7	孟宪佐, 1982 Meng X Z, 1982；孟宪佐等, 1983 Meng X Z et al., 1983
1, 5-戊二醇1, 5-Pentanediol	7	—	Z5, E7;Z5, Z7	Ando et al., 1985
戊醛、(甲酰甲基)三苯基砷盐Valeraldehyde, (Formylmethy1)triphenylarsonium Bromide	4	51	Z5, E7	Huang et al., 1987
乙炔、丙烯醛Ethyne, Acrolein	7	9	Z5, E7	陶云海等, 2005a Tao Y H et al., 2005a
1-溴-顺-2-庚烯的三苯基膦盐、5-乙酰氧戊醛(Z)-2- heptenyl triphenylph osphonium bromide, 5-Acetoxypentanal	1	—	Z, Z;Z, E;E, Z;E, E	Chisholm et al., 1981
1-己炔、2-(4-氯丁氧基)四氢-2H-吡喃1-Hexyne, 2-(4-chlorobutoxy)tetrahydro-2H-pyran	5	31.5	Z5, E7	Ando et al., 1982
1-己炔、5-己炔-1-醇1-Hexyne, 5-Hexyn-1-ol	5	34.4	Z5, E7	Rossi, 1983
1-溴-4-(2-乙氧基乙基)丁烷1-Bromo-4- (2-ethoxyethyl) butane	6	—	Z5, E7	Gardette et al., 1984
1-己炔、5-己炔-1-醇1-Hexyne, 5-Hexyn-1-ol	5	51.7	Z5, E7	Stille et al., 1987
1-己炔、三甲基烯丙基硅烷1-Hexyne, Allyltrimethylsilane	7	—	Z5, E7	孙小静等, 1990 Sune X J et al., 1990
2-(6-庚炔氧基)四氢-2H-吡喃、反-1-碘代己烯2-(6-heptanyloxy)tetrahydro-2H-pyran, (E)-1-Iodo-1-hexene	3	—	Z5, E7	Khrimian et al., 2002
四氢吡喃、1-己炔Tetrahydropyran, 1-Hexyne	9	14.5	Z5, E7	张玉顺, 2001 Zhang Y X, 2001；古昆等, 2004 Gu K et al., 2004
1-己烯、叔丁基(5-己炔氧基)二甲基硅烷1-Hexyne, t-Butyl(5-hexanyloxy) dimethylsilane	4	36.2	Z5, E7	Trost et al., 1984
1-戊炔1-Pentyne	6	—	Z5, E7	Brown et al., 1986
苯基硫代乙炔、铜锂试剂Phenylthioacefylene, Lithium organocuprates	3	57	Z5, E7	Fiandanese et al., 1989
丙炔醇、2-(4-溴丁氧基)四氢-2H-吡喃Propargyl alcohol, 2-(4-BroMobutoxy)terahydro-2H-pyran	7	13.4	Z5, E7	Vig et al., 1990

Table 1

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Table 2

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Research Progress on Total Synthesis of Precursor Components of Sex Pheromones from Six of Pine Caterpillar Species in China

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