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Structure-Odor Correlation, XX. Synthesis and Olfactory Properties of the “Irone-Type Homolog” of Megastigmatrien-3-one

✍ Scribed by Weyerstahl, Peter ;Licha, Kai ;Marschall, Helga

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 420 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419940912

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✦ Synopsis

Abstract

rac‐2‐Methylmegastigma‐4,6,8‐trien‐3‐one (11), the ironetype homolog of the important aroma component megastigmatrien‐3‐one (1), was synthesized starting from 4‐oxoisophorone (2) via 2‐methyl‐4‐oxoisophorone (7) and the ynediol 10 and additionally by methylation of 1. The odor of 11 (tobacco‐like, woody, leathery, plum‐like) is not very different from that of 1.

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Structure-odor correlation, XXV. Synthesis and Olfactory Properties of the “Inverse” Megastigmatrienone and Its Analogs

✍ Weyerstahl, Peter ;Licha, Kai 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 690 KB

## Abstract The oxoisophorone monoacetal 2 is a convenient starting material for the synthesis of several megastigmatrienone analogs. Thus, the Wittig reaction of ketone 2, followed by deprotection, led to the dienones 7–10. The “inverse” megastigmatrienone 1 was synthesized from 2 via homologation