Scientific article
English

Iridoids : enantioselective synthesis of loganin via an asymmetric Diels-Alder reaction

Published inTetrahedron, vol. 42, no. 14, p. 4035-4043
Publication date1986
Abstract

Starting from (-)-camphor-10-sulfonic acid (5) the crystalline sultam 9 was readily prepared. TiCl4-mediated Diels-Alder addition of the N-crotonoyl sultam 11 to cyclopentadiene, crys- tallization of the resulting adduct 12 and subsequent reduction gave virtually pure (1S, 4R, 5R, 6S)-1 together with recovered auxiliary 9. The loganin precursor 1 was transformed into norbornanone 20, which upon Baeyer-Villiger oxidation led to the suitably substituted cyclo- pentane 22 from which 1-B-O-methyl loganin aglucone (2) was readily available.

Citation (ISO format)
VANDEWALLE, M. et al. Iridoids : enantioselective synthesis of loganin via an asymmetric Diels-Alder reaction. In: Tetrahedron, 1986, vol. 42, n° 14, p. 4035–4043. doi: 10.1016/S0040-4020(01)87559-1
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Journal ISSN0040-4020
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