Synthesis 2008(23): 3846-3856  
DOI: 10.1055/s-0028-1083214
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of Novel Polycyclic Heterocycles Using a Tin(II) Chloride Dihydrate-Mediated Deacetalisation-Bicyclisation Sequence

Alex N. Cayleya, Katherine A. Gallaghera, Cécilia Ménard-Moyona, Jan Peter Schmidta, Louis J. Dioraziob, Richard J. K. Taylor*a
a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
b AstraZeneca, Process Research & Development, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK
Further Information

Publication History

Received 12 August 2008
Publication Date:
30 October 2008 (online)

Abstract

Tin(II) chloride dihydrate-mediated deacetalisation-bicyclisation­ procedures for the construction of novel polycyclic heterocycles from amides possessing a pendant acetal group are reported. Optimisation and scoping studies are described; using this methodology, a range of known, and novel, ring-fused heterocyclic systems have been prepared, some in enantiomerically pure form.