Maliha Uroos
Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone
Uroos, Maliha; Pitt, Phillip; Harwood, Laurence; Lewis, William; Blake, Alexander J.; Hayes, Christopher J.
Authors
Phillip Pitt
Laurence Harwood
William Lewis
Alexander J. Blake
CHRIS HAYES chris.hayes@nottingham.ac.uk
Professor of Organic Chemistry
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.
Citation
Uroos, M., Pitt, P., Harwood, L., Lewis, W., Blake, A. J., & Hayes, C. J. (in press). Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone. Organic and Biomolecular Chemistry, 15(40), https://doi.org/10.1039/C7OB02204B
Journal Article Type | Article |
---|---|
Acceptance Date | Sep 21, 2017 |
Online Publication Date | Sep 26, 2017 |
Deposit Date | Oct 3, 2017 |
Publicly Available Date | Sep 27, 2018 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 15 |
Issue | 40 |
DOI | https://doi.org/10.1039/C7OB02204B |
Public URL | https://nottingham-repository.worktribe.com/output/884798 |
Publisher URL | http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB02204B#!divAbstract |
Files
Aritasone OBC_revised 2.pdf
(765 Kb)
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