Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

The scope and limitations of the platinum catalyzed 7-endo cyclization of internal alkynyl amides were investigated. Substitution of the alkyne with an aryl group gave better results, presumably because it stabilized the transition state. Applying the reaction to a secondary amide, the caprazamycin...

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Published inOrganic & biomolecular chemistry Vol. 10; no. 30; pp. 6074 - 6086
Main Authors Tsukano, Chihiro, Yokouchi, Shinsuke, Girard, Anne-Lise, Kuribayashi, Toshifumi, Sakamoto, Shota, Enomoto, Taro, Takemoto, Yoshiji
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.08.2012
Subjects
Alkynes - chemistry
Amides - chemistry
Azepines - chemical synthesis
Azepines - chemistry
Catalysis
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Organic
Cyclization
Physical Sciences
Platinum - chemistry
Science & Technology
REGIOSELECTIVE-SYNTHESIS
LIPOSIDOMYCIN DEGRADATION-PRODUCT
GOLD
RIBOSYL-DIAZEPANONE CORE
INTRAMOLECULAR HYDROAMIDATION
ANALOGS
STEREOSELECTIVE-SYNTHESIS
CONCISE SYNTHESIS
INDOLES
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Summary:The scope and limitations of the platinum catalyzed 7-endo cyclization of internal alkynyl amides were investigated. Substitution of the alkyne with an aryl group gave better results, presumably because it stabilized the transition state. Applying the reaction to a secondary amide, the caprazamycin core was successfully synthesized from commercially available material in eight steps.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25111f