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Paper | Regular issue | Vol 38, No. 9, 1994, pp.2027-2044
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6785
Preparation and Conformational Study of Z-Isositsirikine Model Compounds and Their cis-Nb-Oxides. Determination of the C-16 Configuration

Pirjo Hanhinen, Tomi Nurminen, Reija Jokela,* and Mauri Lounasmaa*

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland

Abstract

Preparation of Z-isositsirikine derivatives (5 - 12) from the allylic alcohols (21) and (22) by the orthoester Claisen rearrangement and their oxidation to the corresponding cis-Nb-oxides (13 - 20) are described. Nmr methods were applied to determine the configuration at C-16 of Z-isositsirikine derivatives and their cis-Nb-oxides. A general, nmr based conformational study of compounds (5 -20) is presented.