Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6 pi-Electrocyclization

Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (mu-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (+/-)-guatambuine, and (+/-)-janetine were developed starting from hexatriene intermediates readily obtained by P...

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Published inEuropean journal of organic chemistry Vol. 2016; no. 13; pp. 2290 - 2299
Main Authors Itoh, Tomoki, Abe, Takumi, Choshi, Tominari, Nishiyama, Takashi, Yanada, Reiko, Ishikura, Minoru
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.05.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIPLASMODIAL ACTIVITY
INDOLYLBORATE
ANTICANCER AGENTS
OLIVACINE
CARBAZOLE ALKALOIDS
Total synthesis
Electrocyclization
Alkaloids
9-METHOXYELLIPTICINE
Nitrogen heterocycles
Natural products
GUATAMBUINE
ELLIPTICINE
INDOLE ALKALOIDS
Copper
DERIVATIVES
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Summary:Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (mu-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (+/-)-guatambuine, and (+/-)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6 pi-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids.
Bibliography:KAKEN
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600246