Novel Rearrangements of Guaiane Sesquiterpenes

Guaiane sesquiterpenes are an important class of biologically active natural products. Several oxygenated bicyclic but also tricyclic derivatives show unprecedented olfactory activity with great importance in perfumery. Their in vivo syntheses are largely controlled by the intrinsic selectivities of...

Full description

Saved in:
Bibliographic Details
Published in:Helvetica chimica acta 2024-02, Vol.107 (2), p.n/a
Main Authors: Türtscher, Paul L., Brunner, Gerhard, Goeke, Andreas
Format: Article
Language:English
Subjects:
Biological activity
Decalin
Dichlorides
Fragrance Chemistry
Guaiane sesquiterpenes
Natural products
NMR
Rearrangement
Rotundone
Sesquiterpenes
Terpenes
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Guaiane sesquiterpenes are an important class of biologically active natural products. Several oxygenated bicyclic but also tricyclic derivatives show unprecedented olfactory activity with great importance in perfumery. Their in vivo syntheses are largely controlled by the intrinsic selectivities of terpene synthases and only a few rearrangements of their hydroazulene skeletons were reported, mostly resulting into terpenoids with decalin motives. Using α‐guaiene and bulnesene, complex rearrangements into novel tri and tetracyclic terpenoids are described herein. The cationic rearrangement mechanisms of their formation based on subsequent 1,2‐H and alkyl shifts promoted by substoichiometric amounts of ethylaluminum dichloride.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202300205