Open AccessTotal Synthesis of Nostodione A, a Cyanobacterial Metabolite
Author(s) -
Andreas Ekebergh,
Anna Börje,
Jerker Mårtensson
Publication year - 2012
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol303036j
Subject(s) - chemistry , total synthesis , intramolecular force , stereoselectivity , indole test , metabolite , stereochemistry , heck reaction , acetic acid , tricyclic , combinatorial chemistry , organic chemistry , catalysis , biochemistry , palladium
The first total synthesis of the mitotic spindle poison nostodione A is described. The inherent oxidative sensitivity of indoles is utilized for a late introduction of a second carbonyl to the cyclopent[b]indole-2-one system. The tricyclic system is prepared from indole-3-acetic acid and O-silylated 4-ethynylphenol, using a stereoselective intramolecular reductive Heck cyclization as the key transformation.
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