Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone

Athula B. Attygalle; Gulab N. Jham; Aleš Svatoš; Rosa T.S. Frighetto; Jerrold Meinwald; Evaldo F. Vilela; Fernando A. Ferrara; Manoel A. Uchôa-Fernandes

doi:10.1016/00404-0399(50)1058P-

Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone

Athula B. Attygalle
, Gulab N. Jham
, Aleš Svatoš
, Rosa T.S. Frighetto
, Jerrold Meinwald
, Evaldo F. Vilela
, Fernando A. Ferrara
, Manoel A. Uchôa-Fernandes

Department of Chemistry and Chemical Biology

Cornell University
Universidade Federal de Viçosa

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

39 Scopus citations

Abstract

The major sex attractant released by Scrobipalpuloides absoluta, a devastating tomato pest, was identified as (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate by a novel strategy involving the random reduction of double bonds. The technique is applicable to double bond localization of polyunsaturated compounds available even in nanogram quantities. The triene ester was synthesized by a stereospecific procedure and shown to be highly attractive to conspecific males and identical to the natural substance.

Original language	English
Pages (from-to)	5471-5474
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	31
DOIs	https://doi.org/10.1016/00404-0399(50)1058P-
State	Published - 31 Jul 1995

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Attygalle, A. B., Jham, G. N., Svatoš, A., Frighetto, R. T. S., Meinwald, J., Vilela, E. F., Ferrara, F. A., & Uchôa-Fernandes, M. A. (1995). Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone. Tetrahedron Letters, 36(31), 5471-5474. https://doi.org/10.1016/00404-0399(50)1058P-

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title = "Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone",

abstract = "The major sex attractant released by Scrobipalpuloides absoluta, a devastating tomato pest, was identified as (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate by a novel strategy involving the random reduction of double bonds. The technique is applicable to double bond localization of polyunsaturated compounds available even in nanogram quantities. The triene ester was synthesized by a stereospecific procedure and shown to be highly attractive to conspecific males and identical to the natural substance.",

author = "Attygalle, \{Athula B.\} and Jham, \{Gulab N.\} and Ale{\v s} Svato{\v s} and Frighetto, \{Rosa T.S.\} and Jerrold Meinwald and Vilela, \{Evaldo F.\} and Ferrara, \{Fernando A.\} and Uch{\^o}a-Fernandes, \{Manoel A.\}",

year = "1995",

month = jul,

day = "31",

doi = "10.1016/00404-0399(50)1058P-",

language = "English",

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AU - Attygalle, Athula B.

AU - Jham, Gulab N.

AU - Svatoš, Aleš

AU - Frighetto, Rosa T.S.

AU - Meinwald, Jerrold

AU - Vilela, Evaldo F.

AU - Ferrara, Fernando A.

AU - Uchôa-Fernandes, Manoel A.

PY - 1995/7/31

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AB - The major sex attractant released by Scrobipalpuloides absoluta, a devastating tomato pest, was identified as (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate by a novel strategy involving the random reduction of double bonds. The technique is applicable to double bond localization of polyunsaturated compounds available even in nanogram quantities. The triene ester was synthesized by a stereospecific procedure and shown to be highly attractive to conspecific males and identical to the natural substance.

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SN - 0040-4039

VL - 36

SP - 5471

EP - 5474

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone

Abstract

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