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Synthetic Applications of the Baylis–Hillman Reaction: Simple and Convenient Synthesis of Five Important Insect Pheromones

✍ Scribed by Biswanath Das; Joydeep Banerjee; Nikhil Chowdhury; Anjoy Majhi; Gurram Mahender

Book ID
102253376
Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
96 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A simple and convenient synthesis of five important insect pheromones by means of Baylis–Hillman adducts is described, i.e., of (2__E__,4__S__)‐2,4‐dimethylhex‐2‐enoic acid (1), a mandibular‐gland secretion of the male carpenter ant in the genus Camponotus, of (+)‐(S)‐manicone (2) and (+)‐(S)‐normanicone (3), two mandibular‐gland constituents of Manica ants, and of (+)‐dominicalure‐I (6) and (+)‐dominicalure‐II (7), two aggregation pheromones of the lesser grain borer Rhyzopertha dominica (F). For the first time, the potential of the Baylis–Hillman chemistry for the stereoselective synthesis of trisubstituted olefins was successfully applied to the synthesis of these pheromone compounds.

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Synthetic Applications of the Baylis–Hil
Synthetic Applications of the Baylis–Hillman Reaction: Simple and Convenient Synthesis of Five Important Insect Pheromones
✍ Biswanath Das; Joydeep Banerjee; Nikhil Chowdhury; Anjoy Majhi; Gurram Mahender 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 German ⚖ 22 KB

On p. 878, lines 6 and 7 should read as follows: In this report, starting from (2S)-2-methylbutanal, we describe a three-step synthesis of (2E,4S)-2,4-dimethylhex-2-enoic acid (1) (obtained in [5c] after six steps) and a 2) On p. 880, line 28 should read as follows: 2. Baylis-Hillman Adducts. Methy