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Highly Selective Oxidations of Fe(CO) 3 ‐Cyclohexadiene Complexes: Synthesis of 4b,8a‐Dihydrocarbazol‐3‐ones and the First Total Synthesis of Carbazomycin A
Author(s) -
Knölker HansJoachim,
Bauermeister Michael,
Bläser Dieter,
Boese Roland,
Pannek JörnBernd
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198902231
Subject(s) - carbazole , stereoselectivity , chemistry , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , catalysis
An approach to the synthesis of highly substituted carbazole derivatives such as 2 and 3 is provided by the iron complex 1 . Depending on the reaction conditions, this compound undergoes stereoselective cyclization to give either the 4a,9a‐dihydro‐ 9H ‐carbazole 2 or the new, analogously substituted 4b,8a‐dihydrocarbazol‐3‐one. This method allows the total synthesis of carbazomycin A 3 . Compound 2 exhibits optical anisotropy, which can be understood in terms of crystal packing.