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Biomimetic Synthesis and Studies Toward Enantioselective Synthesis of Flindersial Alkaloids
Author(s) -
Vallakati Ravikrishna,
Lundy Brian J.,
JansonePopova Santa,
May Jeremy A.
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22134
Subject(s) - enantioselective synthesis , chemistry , biomimetic synthesis , stereochemistry , combinatorial chemistry , organic chemistry , nanotechnology , catalysis , materials science
A strategy allowing both stereocontrol and control over structural isomer formation has been defined for the antimalarial flindersial alkaloids. The recently reported flinderoles were demonstrated to be derived from the natural product borrerine. The structural isomers of flinderoles, the borreverines, were also produced in vitro along with the flinderoles through the dimerization of borrerine in acidic conditions. This result is thought to replicate the biosynthesis of these compounds. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine can each be synthesized in three steps from tryptamine. Furthermore, progress toward a concise enantioselective synthesis of flinderoles A, B, and C is described. This work includes enantioselective conjugate addition to an unprotected indole‐appended enone. Chirality 27:14–17, 2015 . © 2013 Wiley Periodicals, Inc.