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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

Maliha Uroos

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

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