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Divergent Total Synthesis of (±)‐Mahanine and Other Carbazole Alkaloids
Author(s) -
Polley Arghya,
Varalaxmi Kasarla,
Nandi Arijit,
Jana Ranjan
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100176
Subject(s) - carbazole , chemistry , moiety , annulation , total synthesis , ring (chemistry) , pyran , stereochemistry , indole test , murraya , enantioselective synthesis , combinatorial chemistry , suzuki reaction , organic chemistry , palladium , catalysis , botany , biology
We represent here, a divergent approach for the total synthesis of (±)‐Mahanine and twelve other naturally occurring carbazole alkaloids. Remarkably, we have utilized a simplified scalable Suzuki coupling for C−C bond formation and a metal‐free C−N coupling sequence to synthesize the functionalized carbazole scaffold from a single intermediate. Subsequently, either functional group manipulations or late‐stage pyran ring annulation furnished a library of 13 carbazole alkaloids mostly isolated from a traditional medicinal plant Murraya koenigii . The construction of carbazole moiety at the initial‐stage followed by late‐stage pyran annulation under mild condition overcomes the decomposition problem of pyran‐ring under acidic or other harsh reaction conditions.