𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and Properties of Conformationally Constrained Analogues of Floral-Type Odorants

✍ Scribed by Serge Lamboley; Cédric Morel; Jean-Yves de Saint Laumer; André F. Boschung; Nigel G. J. Richards; Béat M. Winter

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
677 KB
Volume
87
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The twelve bridged analogues 8–19 of floral‐type odorants related to cyclamenaldehyde (1) were synthesized (Schemes 1–5) to investigate the relationship between the structural and conformational features of these compounds and their odor properties. Comparison of the data from sensory evaluation and molecular modeling suggests that the side chain of both the unconstrained and the constrained active analogues is not extended (anti) but rather folded (gauche) in the ‘bioactive’ conformation. However, it is mainly the nature of the substituents at the α position of the aldehyde function that critically influences the odor quality and strength. These studies provide new information that should aid ongoing efforts to develop models of odorantreceptor interactions.

📜 SIMILAR VOLUMES

Azabicycloalkenes as Synthetic Intermedi
Azabicycloalkenes as Synthetic Intermediates – Synthesis of Conformationally Constrained Glutamate Analogues
✍ Wolfgang Maison 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 177 KB

## Abstract As a part of our study of the cancer‐specific protease PSMA (prostate‐specific membrane antigen) we present a stereoselective synthesis of conformationally constrained glutamate mimetics. Key intermediates are azabicycloalkenes which are synthesized via diastereoselective or enantiosele