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Configurational analysis of the natural product passifloricin A by quantum mechanical 13C NMR GIAO chemical shift calculations

✍ Scribed by Giuseppe Bifulco; Luigi Gomez-Paloma; Raffaele Riccio

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 310 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01810-0

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✦ Synopsis

Quantum chemical calculations at mPW1PW91 level, with full geometry optimization, using the 6-31g(d) basis set, and GIAO (gauge including atomic orbitals) 13 C NMR chemical shifts using the 6-31g(d,p) basis set, are here utilized as a support to define the configurational features of the natural product passifloricin A, whose previously proposed relative configuration has been recently shown, by synthetic studies, to be incorrect. This study suggests that the relative stereostructure for passifloricin A corresponds to the d-lactone of the (5R,7R,9S,11R)-tetrahydroxyhexacos-2-enoic acid.

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