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Hydroazulene derivatives, III. Enantioselective synthesis of a highly functionalized perhydroazulene
Author(s) -
Schäfer HansJürgen,
Baringhaus KarlHeinz
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900168
Subject(s) - chemistry , enantioselective synthesis , aldehyde , intramolecular force , lewis acids and bases , lactone , diol , stereochemistry , catalysis , combinatorial chemistry , organic chemistry
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.