Efficient synthesis of beetle aggregation pheromone frontalin and its analogues

Xiaobao Yang; Shengjun Luo; Chengwen Hua; Hongbin Zhai

doi:10.1016/j.tet.2003.09.029

Efficient synthesis of beetle aggregation pheromone frontalin and its analogues

Xiaobao Yang
, Shengjun Luo
, Chengwen Hua
, Hongbin Zhai

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

(-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.

Original language	English
Pages (from-to)	8551-8553
Number of pages	3
Journal	Tetrahedron
Volume	59
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2003.09.029
State	Published - 20 Oct 2003
Externally published	Yes

Keywords

Aggregation pheromone
Double dihydroxylation
Frontalin
Intramolecular acetalation
Synthesis

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10.1016/j.tet.2003.09.029

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@article{20436d59467b461d8ac11ab1b30ed432,

title = "Efficient synthesis of beetle aggregation pheromone frontalin and its analogues",

abstract = "(-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64\% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.",

keywords = "Aggregation pheromone, Double dihydroxylation, Frontalin, Intramolecular acetalation, Synthesis",

author = "Xiaobao Yang and Shengjun Luo and Chengwen Hua and Hongbin Zhai",

note = "Funding Information: We thank the following agencies for financial support: Chinese Academy of Sciences ({\textquoteleft}Hundreds of Talent{\textquoteright} Program); Science \& Technology Commission of Shanghai Municipality ({\textquoteleft}Venus{\textquoteright} Program); National Natural Science Foundation of China (20102008).",

year = "2003",

month = oct,

day = "20",

doi = "10.1016/j.tet.2003.09.029",

language = "English",

volume = "59",

pages = "8551--8553",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "43",

}

TY - JOUR

T1 - Efficient synthesis of beetle aggregation pheromone frontalin and its analogues

AU - Yang, Xiaobao

AU - Luo, Shengjun

AU - Hua, Chengwen

AU - Zhai, Hongbin

N1 - Funding Information: We thank the following agencies for financial support: Chinese Academy of Sciences (‘Hundreds of Talent’ Program); Science & Technology Commission of Shanghai Municipality (‘Venus’ Program); National Natural Science Foundation of China (20102008).

PY - 2003/10/20

Y1 - 2003/10/20

N2 - (-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.

AB - (-)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as 4a and 4b.

KW - Aggregation pheromone

KW - Double dihydroxylation

KW - Frontalin

KW - Intramolecular acetalation

KW - Synthesis

UR - https://www.scopus.com/pages/publications/0141594840

U2 - 10.1016/j.tet.2003.09.029

DO - 10.1016/j.tet.2003.09.029

M3 - Article

AN - SCOPUS:0141594840

SN - 0040-4020

VL - 59

SP - 8551

EP - 8553

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

Efficient synthesis of beetle aggregation pheromone frontalin and its analogues

Abstract

Keywords

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