Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone

Uroos, Maliha and Pitt, Phillip and Harwood, Laurence and Lewis, William and Blake, Alexander J. and Hayes, Christopher J. (2017) Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone. Organic and Biomolecular Chemistry . ISSN 1477-0539

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Abstract

This paper describes a total synthesis of the terpene-derived natural product aritasone via the hetero-Diels-Alder [4+2] cyclodimerisation of pinocarvove, which represents the proposed biosyntheic route. The hetero-Diels-Alder dimerisation of pinocarvone did not proceed under standard conditions, and ultra-high pressure (19.9 kbar) was required. As it seems unlikely that these ultra-high pressures are accessible within a plant cell, we suggest that the original biosynthetic hypothesis be reconsidered, and alternatives are discussed.

Item Type: Article
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1039/C7OB02204B
Depositing User: Hayes, Chris
Date Deposited: 03 Oct 2017 08:09
Last Modified: 18 Oct 2017 18:54
URI: http://eprints.nottingham.ac.uk/id/eprint/46603

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