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Issue 15, 2017
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cis or trans with class II diterpene cyclases

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Abstract

Isoprenoid precursors readily undergo (poly)cyclization in electrophilic reaction cascades, presumably as internal addition of the carbon–carbon double-bonds from neighboring isoprenyl repeats readily forms relatively stable cyclohexyl tertiary carbocation intermediates. This hypothesis is agnostic regarding alkene configuration (i.e., Z or E). Consistent with this, here it is shown that certain class II diterpene cyclases, which normally convert (E,E,E)-geranylgeranyl diphosphate to 13E-trans-decalin bicycles, will also act upon (Z,Z,Z)-nerylneryl diphosphate, producing novel 13Z-cis-decalin bicycles instead.

Graphical abstract: cis or trans with class II diterpene cyclases

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Publication details

The article was received on 28 Feb 2017, accepted on 21 Mar 2017 and first published on 21 Mar 2017


Article type: Communication
DOI: 10.1039/C7OB00510E
Citation: Org. Biomol. Chem., 2017,15, 3158-3160

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    cis or trans with class II diterpene cyclases

    M. Jia and R. J. Peters, Org. Biomol. Chem., 2017, 15, 3158
    DOI: 10.1039/C7OB00510E

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