Tetrahedron p. 4035 - 4044 (1986)
Update date:2022-08-03
Topics:
Vandewalle, M.
Van der Eycken, J.
Oppolzer, W.
Vullioud, C.
Starting from (-)-camphor-10-sulfonic acid (5) the crystalline sultam 9 was readily prepared.TiCl4-mediated Diels-Alder addition of the N-crotonyl sultam 11 to cyclopentadiene, crystallization of the resulrting 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 norbonanone 20, which upon Baeyer-Villiger oxidation led to the suitably substituted cyclopentane 22 from which 1-B-O-methyl loganin aglucone (2) was readily available.
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