TMSI-Mediated Prins Cyclization: Diastereoselective Synthesis of 4-Iodo-2,6-Disubstituted Tetrahydropyrans and Synthesis of (±)-Centrolobine

TMSI-Mediated Prins Cyclization: Diastereoselective Synthesis of 4-Iodo-2,6-Disubstituted Tetrahydropyrans and Synthesis of (±)-Centrolobine

Abstract The reaction of aldehydes with homoallyl alcohols in the presence of TMSI generated in situ from TMSCl and NaI produced 4-iodo-tetrahydropyrans in good yields as a mixture of diastereo­isomers, which are separated and characterized. These iodo pyrans are reported for the first time. This me...

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Veröffentlicht in:Synlett 2005-09, Vol.2005 (15), p.2347-2351
Hauptverfasser: Sabitha, Gowravaram, Reddy, K. Bhaskar, Reddy, G. S., Fatima, Narjis, Yadav, J. S.
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Sprache:eng
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Zusammenfassung:Abstract The reaction of aldehydes with homoallyl alcohols in the presence of TMSI generated in situ from TMSCl and NaI produced 4-iodo-tetrahydropyrans in good yields as a mixture of diastereo­isomers, which are separated and characterized. These iodo pyrans are reported for the first time. This methodology was extended to the synthesis of (±)-centrolobine.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-872668