Diastereoselective Synthesis of Tricyclo[3.2.1.0]octanes; Chiral Building Blocks for Terpenes

Publication Type
Journal contribution
Authors
Braun, N. A.; Klein, I.; Spitzner, D.;Vogler B.; Borrmann, H.; Simon, A.
Year of publication
1995
Published in
Tetrahedron Letters
Band/Volume
36/21
Page (from - to)
3675-3678
Abstract

One pot cascade reactions of 3-benzyloxy-cyclohex-2-enone with tert-butyl-(Z)-(+)-2-chloro- 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]- 2-propenoate [(+)-(Z)-I] lead to (1S;2R;5S;7S;8R;4'S)-tert-butyl-2- benzyloxy-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-oxo-tricyclo[3.2.1.02,7]octane-1-carboxylate (II) and with (E)-(+)-I to (1R;2R;5R;7R;8S;4'S)-III. The tricyclic compds. II and III were formed with high diastereomeric excess.

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