Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

Jacqueline Poldy; Rod Peakall; Russell A. Barrow

doi:10.1016/j.tetlet.2008.02.037

Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

Jacqueline Poldy, Rod Peakall, Russell A. Barrow^*

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

Original language	English
Pages (from-to)	2446-2449
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.037
Publication status	Published - 7 Apr 2008

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10.1016/j.tetlet.2008.02.037

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title = "Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones",

abstract = "Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.",

keywords = "Chiloglottis, Cyclohexanedione, Neozeleboria, Organocadmium reagents, Pheromone, Sexual deception",

author = "Jacqueline Poldy and Rod Peakall and Barrow, {Russell A.}",

year = "2008",

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language = "English",

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T1 - Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them

T2 - a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

AU - Poldy, Jacqueline

AU - Peakall, Rod

AU - Barrow, Russell A.

PY - 2008/4/7

Y1 - 2008/4/7

N2 - Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

AB - Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

KW - Chiloglottis

KW - Cyclohexanedione

KW - Neozeleboria

KW - Organocadmium reagents

KW - Pheromone

KW - Sexual deception

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DO - 10.1016/j.tetlet.2008.02.037

M3 - Article

SN - 0040-4039

VL - 49

SP - 2446

EP - 2449

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

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