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Construction of the Cyclopenta[1,3]cyclopropa[1,2‐ b ]naphthalene System in a One‐Pot Domino Reaction
Author(s) -
Krohn Karsten,
Freund Christian,
Flörke Ulrich
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199812)1998:12<2713::aid-ejoc2713>3.0.co;2-g
Subject(s) - chemistry , domino , naphthalene , yield (engineering) , cascade reaction , condensation reaction , medicinal chemistry , base (topology) , condensation , reaction conditions , stereochemistry , organic chemistry , catalysis , mathematical analysis , materials science , physics , mathematics , metallurgy , thermodynamics
Base treatment of the angucycline oligoketide precursor 6 unexpectedly afforded the spirocyclization product 7 . An additional step in the domino cyclization process was observed starting from the quinoid bromo diketone 3b to yield stereospecifically the condensed tetracycle 8 with the benzo‐annelated skeleton of the cubebol‐typeterpenes. The structure of 8 was confirmed by X‐ray structure analysis. Further extension of the domino sequence by reaction of the dibromide 10 with acetonedicarboxylic ester 11 gave the cyclization/condensation products 12 , 13 , or 14 , depending on the reaction conditions.