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Formal synthesis of schulzeines B and C: A new route to Gurjar's lactams
Author(s) -
Chou ChuEn,
Chen YiAn,
Lin YiChing,
Kao ShihChieh,
Chang ChiehYu,
Wu YenKu
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000216
Subject(s) - chemistry , annulation , sequence (biology) , continuous flow , convergent synthesis , stereochemistry , coupling (piping) , formal synthesis , lactam , nucleus , combinatorial chemistry , organic chemistry , catalysis , biochemistry , biochemical engineering , mechanical engineering , engineering , biology , microbiology and biotechnology
Described is a formal synthesis of racemic schulzeines B and C that intercepts intermediates developed by Gurjar and co‐workers. The synthetic sequence features an annulative coupling of a ketimine and acrylic acid enabling the construction of the benzoquinolizidine nucleus in a highly convergent manner. We also examined a continuous‐flow version of the thermal aza‐annulation, which proved less practical as compared to the batch processes.