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.

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
• Contract Date: Oct 3, 2017