Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvoneTools 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 Full text not available from this repository.AbstractThis 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.
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