NMR structure determination and intramolecular transesterification of four diacetyl taxinines which co-elute with taxol obtained from Taxus x. media Hicksi needles

Add time:09/03/2019    Source:sciencedirect.com

The isolation of taxol from Taxus x. media Hicksii includes four taxinines which co-elute and interfere with HPLC analyses of taxol. Their structures: 1,9α-dihydroxy-2α,10β-diacetoxy-5α-cinnamatetaxa-4(20),11-diene-13-one; 1,10β-dihydroxy-2α,9α-diacetoxy-5α-cinnamatetaxa-4(20),11-diene-13-one;2α,9α-dihydroxy-10β,13α-diacetoxy-5α-cinnamatetaxa-4(20),11-diene and; 2α,10β-dihydroxy-9α,13α-diacetoxy-5α-cinnamatetaxa-4(20),11-diene, have been determined by 1D(1H, 13C) and 2D(DQCOSY, TOCSY, HMQC, HMBC and TROESY) NMR spectroscopy-Transacetylation between 10β and 9α on the baccatin core has been documented to occur in CDCl3 and CD3OD at 27°. Interatomic distances were obtained from TROESY build-up curves of the compound and were compare to those obtained from a computer minimized structure.

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