69 research outputs found

    Iridoids : enantioselective synthesis of loganin via an asymmetric diels-alder reaction

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    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 rea- dily available

    Fully selective intramolecular ortho photocycloaddition of 4-(4-methoxyphenoxy)-3-(N3-benzoylthymin-1-yl)but-1-ene: An unprecedented benzene-thymine photocycloaddition

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    On irradiation of 4-(4-methoxyphenoxy)-3-(N-3-benzozylthymin-1-yl)but-1-ene 1 at 254 nm in THF a single photoadduct 2 is formed as a result of chemo-, regio- and stereo-selective intramolecular ortho photocycloaddition of the thymine double bond to the 1,2-positions of the phenyl ring.status: publishe
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