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

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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.

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

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Publication details

The article was received on 01 Sep 2017, accepted on 21 Sep 2017 and first published on 26 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02204B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone

    M. Uroos, P. Pitt, L. M. Harwood, W. Lewis, A. J. Blake and C. J. Hayes, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02204B

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