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Hydroazulene derivatives, III. Enantioselective synthesis of a highly functionalized perhydroazulene

✍ Scribed by Schäfer, Hans-Jürgen ;Baringhaus, Karl-Heinz

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
681 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

A synthesis of the enantiomerically pure perhydroazulene 19 is reported. 19 gives rise to homochiral guaianolides. Lactone 3 serves as starting material and is first converted into the diol 12 by two different consecutive alkylations. Subsequent functional group transformations generate the aldehyde 17, and Lewis acid catalyzed intramolecular cyclization produces 19. Configuration and stereochemistry of 19 have been determined by spectroscopic means in combination with force‐field calculations.

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