Ultrasound assisted synthesis of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane - the sex pheromones of Leucoptera coffeella

Nhuan Ngoc Doan; Thach Ngoc Le; Hao Cong Nguyen; Poul Erik Hansen; Fritz Duus

doi:10.3390/12082080

Ultrasound assisted synthesis of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane - the sex pheromones of Leucoptera coffeella

Nhuan Ngoc Doan
, Thach Ngoc Le
, Hao Cong Nguyen
, Poul Erik Hansen
, Fritz Duus^*

^*Corresponding author

Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

12 Citations (Scopus)

5 Downloads (Pure)

Abstract

Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps).

Original language	English
Journal	Molecules
Volume	12
Issue number	8
Pages (from-to)	2080-2088
Number of pages	9
ISSN	1420-3049
DOIs	https://doi.org/10.3390/12082080
Publication status	Published - Aug 2007

Keywords

5,9-Dimethylhexadecane
5,9-Dimethylpentadecane
Leucoptera coffeella
Pheromones
Ultrasound irradiation

Access to Document

10.3390/12082080Licence: CC BY

Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeellaFinal published version, 70.3 KBLicence: CC BY

OpenUrl availability

Full text

Citation Styles

@article{d478b20bc62a48289fae21384fe7a2ab,

title = "Ultrasound assisted synthesis of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane - the sex pheromones of Leucoptera coffeella",

abstract = "Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58\% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps).",

keywords = "5,9-Dimethylhexadecane, 5,9-Dimethylpentadecane, Leucoptera coffeella, Pheromones, Ultrasound irradiation, 5,9-Dimethylhexadecane, 5,9-Dimethylpentadecane, Leucoptera coffeella, Pheromones, Ultrasound irradiation",

author = "Doan, \{Nhuan Ngoc\} and Le, \{Thach Ngoc\} and Nguyen, \{Hao Cong\} and Hansen, \{Poul Erik\} and Fritz Duus",

year = "2007",

month = aug,

doi = "10.3390/12082080",

language = "English",

volume = "12",

pages = "2080--2088",

journal = "Molecules",

issn = "1420-3049",

publisher = "M D P I AG",

number = "8",

}

TY - JOUR

T1 - Ultrasound assisted synthesis of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane - the sex pheromones of Leucoptera coffeella

AU - Doan, Nhuan Ngoc

AU - Le, Thach Ngoc

AU - Nguyen, Hao Cong

AU - Hansen, Poul Erik

AU - Duus, Fritz

PY - 2007/8

Y1 - 2007/8

N2 - Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps).

AB - Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps).

KW - 5,9-Dimethylhexadecane

KW - 5,9-Dimethylpentadecane

KW - Leucoptera coffeella

KW - Pheromones

KW - Ultrasound irradiation

KW - 5,9-Dimethylhexadecane

KW - 5,9-Dimethylpentadecane

KW - Leucoptera coffeella

KW - Pheromones

KW - Ultrasound irradiation

U2 - 10.3390/12082080

DO - 10.3390/12082080

M3 - Journal article

C2 - 17960107

AN - SCOPUS:34548458102

SN - 1420-3049

VL - 12

SP - 2080

EP - 2088

JO - Molecules

JF - Molecules

IS - 8

ER -