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Synthesis 2016; 48(13): 2130-2136
DOI: 10.1055/s-0035-1561588
DOI: 10.1055/s-0035-1561588
paper
Chemoenzymatic Access to (+)-Artabotriol and its Application in Collective Synthesis of (+)-Grandiamide D, (–)-Tulipalin B, (+)-Spirathundiol, and (+)-Artabotriolcaffeate
Further Information
Publication History
Received: 22 January 2016
Accepted after revision: 24 February 2016
Publication Date:
12 April 2016 (online)
Abstract
Starting from dimethyl (±)-2-hydroxy-3-methylenesuccinnate chemoenzymatic collective formal/total synthesis of enantiomerically pure bioactive natural products has been described via the advanced level common precursor (+)-artabotriol. An efficient enzymatic resolution with high enantiomeric purity, selective diester to diol reduction, and requisite dehydrative coupling reactions without any racemization are the significant topographies.
Key words
dimethyl (±)-2-hydroxy-3-methylenesuccinate - enzymatic resolution - reduction - (+)-artabotriol - coupling reactions - collective synthesis - natural productsSupporting Information
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1H NMR, 13C NMR and DEPT spectra of compounds 1–9 and 12–15 as well as HPLC data for the enantiomeric purity of the compounds 1, 2, and 9 are available free of charge online at http://dx.doi.org/10.1055/s-0035-1561588.
- Supporting Information
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