An efficient total synthesis of ruprechstyril from Ruprechtia tangarana.

Abstract:

:A short total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone) isolated from Ruprechtia tangarana is reported. 6,8-Dimethoxy-3-pentylisocoumarin obtained by condensation of 3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride was smoothly converted to O-methylruprechstyril by refluxing with methanamide. Regioselective demethylation of the latter using anhydrous aluminium chloride in dichloromethane furnished the ruprechstyril. Complete demethylation to give (6-desmethoxyruprechstyril) was achieved using same reagent in ethanethiol.

journal_name

Nat Prod Res

journal_title

Natural product research

authors

Saeed A

doi

10.1080/14786419.2012.715292

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

1153-8

issue

13

eissn

1478-6419

issn

1478-6427

journal_volume

27

pub_type

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