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Title: Stereoselective synthesis of trans-fused tetrahydrofuran derivatives of 5H-dibenzo[a,d]cycloheptene
Authors: Compernolle, Frans ×
Mao, Hua
Tahri, A
Kozlecki, Tomasz
Van der Eycken, Erik
Medaer, B
Hoornaert, GJ #
Issue Date: Jan-2002
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron letters vol:43 issue:16 pages:3011-3015
Abstract: The epoxides derived from 5H-dibenzo[a.d]cycloheptene and its 2-fluoro derivative were converted to trans-fused hydrofurans 4a.b (55 and 44% overall fields) via a five-step sequence. i.e. (i) epoxide ring opening using propargylmagnesium bromide. (ii) mercury(II)-induced cyclisation and in situ bromination to give the bromomethylene substituted hydrofurans, (iii, iv) acid catalysed hydration and stereoselective reduction of the hemiacetal intermediates, and (v) base promoted cyclisation. (C) 2002 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4039
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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