An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta
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Source and publish data:
Synthesis p. 961 - 968 (2015)
Update date:2022-08-29
Topics:
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Authors:
Puigmartí, Marc
Bosch, Ma Pilar
Guerrero, Angel
Article abstract of DOI:10.1055/s-0034-1379977
A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.
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Full text of DOI:10.1055/s-0034-1379977
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Supporting Information
for DOI: 10.1055/s-0034-1379977
© Georg Thieme Verlag KG Stuttgart · New York 2015
Thieme
SUPPORTING INFORMATION
An improved and convenient new synthesis of the pheromone
components of the tomato leafminer Tuta absoluta
Marc Puigmartí, Mª Pilar Bosch and Angel Guerrero*
Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of
Catalonia (CSIC), Jordi Girona 18. 08034 Barcelona, Spain.
Fax: +34 932045904
Content
1
1. Copy of H and 13C NMR spectra of all compounds and HRMS of compounds 12, 17, 18
and elemental analysis of compounds 1, 2.
1
1-(Methoxymethyloxy)-4,7-decadiyne (4)
1-(Methoxymethyloxy)-4,7-decadiyne (4)
2
(4Z,7Z)-1-(Methoxymethyloxy)-4,7-decadiene (5)
(4Z,7Z)-1-(Methoxymethyloxy)-4,7-decadiene (5)
3
(4Z,7Z)-4,7-Decadien-1-ol (6)
(4Z,7Z)-4,7-Decadien-1-ol (6)
4
(4Z,7Z)-1-Bromo-4,7-decadiene (7)
(4Z,7Z)-1-Bromo-4,7-decadiene (7)
5
1-(Tetrahydropyran-2-yloxy)-3-butyne (8)
1-(Tetrahydropyran-2-yloxy)-3-butyne (8)
6
(8Z,11Z)-1-(Tetrahydropyran-2-yloxy)-8,11-tetradecadien-3-yne (9)
(8Z,11Z)-1-(Tetrahydropyran-2-yloxy)-8,11-tetradecadien-3-yne (9)
7
(3E,8Z,11Z)-1-(Tetrahydropyran-2-yloxy)-3,8,11-tetradecatriene (10a)
(3E,8Z,11Z)-1-(Tetrahydropyran-2-yloxy)-3,8,11-tetradecatriene (10a)
8
(3E,8Z,11Z)-3,8,11-Tetradecatrien-1-ol (11)
(3E,8Z,11Z)-3,8,11-Tetradecatrien-1-ol (11)
9
(3E,8Z,11Z)-3,8,11-Tetradecatrienyl acetate (1)
(3E,8Z,11Z)-3,8,11-Tetradecatrienyl acetate (1)
10
(3E,8Z,11Z)-3,8,11-Tetradecatrienyl acetate (1)
11
1-(Methoxymethyloxy)-4-decyne (12)
1-(Methoxymethyloxy)-4-decyne (12)
12
1-(Methoxymethyloxy)-4-decyne (12)
13
4-Decyn-1-ol (13)
4-Decyn-1-ol (13)
14
(Z)-4-Decen-1-ol (14)
(Z)-4-Decen-1-ol (14)
15
(4Z)-1-Iodo-4-decene (15)
(4Z)-1-Iodo-4-decene (15)
16
1-t-Butyldimethylsilyloxy-3-butyne (16)
1-t-Butyldimethylsilyloxy-3-butyne (16)
17
(8Z)-1-t-Butyldimethylsilyloxy-8-tetradecen-3-yne (17)
(8Z)-1-t-Butyldimethylsilyloxy-8-tetradecen-3-yne (17)
18
(8Z)-1-t-Butyldimethylsilyloxy-8-tetradecen-3-yne (17)
0 . 3
(3E,8Z)-1-t-Butyldimethylsilyloxy-3,8-tetradecadiene (18)
- 2 . 2
19
(3E,8Z)-1-t-Butyldimethylsilyloxy-3,8-tetradecadiene (18)
(3E,8Z)-1-t-Butyldimethylsilyloxy-3,8-tetradecadiene (18)
20
(3E,8Z)-Tetradeca-3,8-dien-1-ol (19)
(3E,8Z)-Tetradeca-3,8-dien-1-ol (19)
21
(3E,8Z)-Tetradeca-3,8-dien-1-yl acetate (2)
(3E,8Z)-Tetradeca-3,8-dien-1-yl acetate (2)
22
(3E,8Z)-Tetradeca-3,8-dien-1-yl acetate (2)
23