Stereodivergent Synthesis of
the C1-C9 Tetrahydropyran Subunit of Zincophorin
and Isomers Thereof

François Godin; Ioannis Katsoulis; Émilie Fiola-Masson; Sabrina Dhambri; Philippe Mochirian; Yvan Guindon

doi:10.1055/s-0031-1289661

PAPER

Stereodivergent Synthesis of the C1-C9 Tetrahydropyran Subunit of Zincophorin and Isomers Thereof

François Godin^a,b, Ioannis Katsoulis^a, Émilie Fiola-Masson^a, Sabrina Dhambri^a, Philippe Mochirian^a,b, Yvan Guindon*^a,b,c
^a Institut de recherches cliniques de Montréal (IRCM), Bioorganic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, QC, H2W 1R7, Canada
Fax: +1(514)9875789; e-Mail: yvan.guindon@ircm.qc.ca;
^b Department of Chemistry, Université de Montréal, C.P. 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada
^c Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montréal, QC, H3A 2K6, Canada

Abstract

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Abstract

Zincophorin C1-C9 fragment and seven tetrahydropyran analogues were prepared diastereoselectively by sequential iodoetherification and radical hydrogen-transfer reactions. Stereoselective formation of 3,7-trans or 3,7-cis rings was rationalized through minimization of allylic-1,3 strain in chair-like transition states. Subsequent hydrogen-transfer provided 7,8-anti or 7,8-syn isomers under acyclic stereocontrol or endocyclic control respectively. The latter approach relies on the formation of a [4.4.0] bicyclic complexes resulting from the chelation of the oxygen of the tetrahydropyran ring and the ester by a bidentate Lewis acid.

Key words

ionophore - iodoetherification - radical reduction - Lewis acid - substituted tetrahydropyrans

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