2-Thioindoles as precursors to spiro-fused indolines: Synthesis of (±)-dehaloperophoramidine

Angewandte Chemie - International Edition

Volumn 45, Issue 26, 2006, Pages 4317-4320

  Sabahi, Amir ^a   Novikov, Alexei ^a   Rainier, Jon D ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Communesin; Cyclization; Natural products; Perophoramidine; Thioindoles

Indexed keywords

COMMUNESIN; CYCLIZATION; NATURAL PRODUCTS; PEROPHORAMIDINE; THIOINDOLES;

CHLORINE COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

COMMUNESIN B; FUSED HETEROCYCLIC RINGS; HALOGENATED HYDROCARBON; INDOLE DERIVATIVE; INDOLINE; PEROPHORAMIDINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS;

EID: 33746280887     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601278     Document Type: Article

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19. We also explored a number of other basic and acidic conditions without success.
20. An examination of molecular models of 21 and 24 indicates that approach of the amine onto the C24 imidate carbon is blocked by the C18 proton; the formation of 25 allows the aromatic ring to rotate, thus alleviating this problem.
21. When the aminal was protected with a Boc group, reductive removal of the benzyl group resulted in the decomposition of the perophoramidine ring system.