Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone
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, a...
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| Format: | Article |
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Royal Society of Chemistry
2017
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| Online Access: | https://eprints.nottingham.ac.uk/46603/ |
| _version_ | 1848797365356462080 |
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| author | Uroos, Maliha Pitt, Phillip Harwood, Laurence Lewis, William Blake, Alexander J. Hayes, Christopher J. |
| author_facet | Uroos, Maliha Pitt, Phillip Harwood, Laurence Lewis, William Blake, Alexander J. Hayes, Christopher J. |
| author_sort | Uroos, Maliha |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:02:43Z |
| format | Article |
| id | nottingham-46603 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:43Z |
| publishDate | 2017 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-466032020-05-04T19:08:51Z https://eprints.nottingham.ac.uk/46603/ 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. 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. Royal Society of Chemistry 2017-09-26 Article PeerReviewed Uroos, Maliha, Pitt, Phillip, Harwood, Laurence, Lewis, William, 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, 15 (40). pp. 8523-8538. ISSN 1477-0539 http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB02204B#!divAbstract doi:10.1039/C7OB02204B doi:10.1039/C7OB02204B |
| spellingShingle | Uroos, Maliha Pitt, Phillip Harwood, Laurence Lewis, William Blake, Alexander J. Hayes, Christopher J. Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title | Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title_full | Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title_fullStr | Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title_full_unstemmed | Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title_short | Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone |
| title_sort | total synthesis of (−)-aritasone via the ultra-high pressure hetero-diels–alder dimerisation of (−)-pinocarvone |
| url | https://eprints.nottingham.ac.uk/46603/ https://eprints.nottingham.ac.uk/46603/ https://eprints.nottingham.ac.uk/46603/ |