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Decagram‐Scale Synthesis of the Neocarzinostatin Carboxylic Acid
Author(s) -
Görth Felix Christian,
Rucker Mark,
Eckhardt Matthias,
Brückner Reinhard
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:14<2605::aid-ejoc2605>3.0.co;2-y
Subject(s) - chemistry , decarboxylation , regioselectivity , hydrolysis , yield (engineering) , cinnamic acid , carboxylic acid , organic chemistry , double bond , acrylate , medicinal chemistry , catalysis , materials science , polymer , monomer , metallurgy
Neocarzinostatin carboxylic acid ( 2 ) was synthesized on a 10‐g scale in 9 steps and 43% overall yield from 3,5‐dimethylanisol ( 9 ) (Schemes 5, 7). The hindered bromoarene 23 , reached after 3 steps, underwent a high‐temperature Heck coupling with ethyl acrylate, generating cinnamic ester 24 . The C=C bond was reduced and the C≡N group methanolized to obtain diester 30 . This underwent a regioselective Dieckmann cyclization, furnishing the dihydronaphthalene 13 , that was then aromatized. The resulting ester 31 was carefully hydrolyzed such that the target acid 2 arose free from decarboxylation product 32 .