Synthetic Studies on Potent Marine Drugs: Synthesis and the Crystal Structure of 6‐ tert ‐butyl‐4‐phenyl‐4 H ‐chromene‐2‐carboxylic Acid

4 H ‐Chromene‐2‐carboxylic acid ester derivatives of renieramycin M might be of use for the structural‐activity relationship studies of antitumor antibiotic tetrahydroisoquinoline natural products. Accordingly, 6‐ tert ‐butyl‐4‐phenyl‐4 H ‐chromene‐2‐carboxylic acid, one key intermediate, was synthe...

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Published inJournal of chemistry Vol. 2013; no. 1
Main Authors Li, Hui-Jing, Wang, Jun-Li, Wang, Rui, Luo, Dong-Hui, Wu, Yan-Chao
Format Journal Article
LanguageEnglish
Published 01.01.2013
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Summary:4 H ‐Chromene‐2‐carboxylic acid ester derivatives of renieramycin M might be of use for the structural‐activity relationship studies of antitumor antibiotic tetrahydroisoquinoline natural products. Accordingly, 6‐ tert ‐butyl‐4‐phenyl‐4 H ‐chromene‐2‐carboxylic acid, one key intermediate, was synthesized via the condensation of (3 E )‐2‐oxo‐4‐phenylbut‐3‐enoate methyl ester with 4‐ tert ‐butylphenol in the presence of AuCl 3 /3AgOTf (5 mol%), followed by cyclodehydration and aqueous hydrolysis. The product was unambiguously shown to the 4 H ‐chromene‐2‐carboxylic acid by spectroscopy and X‐ray crystallographic analysis. A packing diagram of the crystal structure shows that aromatic π ‐stacking interactions and O–H ⋯ O hydrogen bond stabilize the structure in the solid.
ISSN:2090-9063
2090-9071
DOI:10.1155/2013/106908