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One-pot synthesis of 6-hydroxyisochromans: the example of demethyl-oxa-coclaurine (Articolo in rivista)
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- One-pot synthesis of 6-hydroxyisochromans: the example of demethyl-oxa-coclaurine (Articolo in rivista) (literal)
- Anno
- 2003-01-01T00:00:00+01:00 (literal)
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M.GUISO, A.BIANCO, C.MARRA, C.CAVARISCHIA (2003)
One-pot synthesis of 6-hydroxyisochromans: the example of demethyl-oxa-coclaurine
in European journal of organic chemistry (Print)
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- M.GUISO, A.BIANCO, C.MARRA, C.CAVARISCHIA (literal)
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- Titolo
- One-pot synthesis of 6-hydroxyisochromans: the example of demethyl-oxa-coclaurine (literal)
- Abstract
- Using a modified oxa-Pictet Spengler reaction that we recently described, we synthesized 6-hydroxy-isochromans and their 7-hydroxy derivatives. The synthesis, which consists of one step and does not require protecting groups, was successful and provided high yields. The obtainment of 1-(4'-hydroxy-benzyl)-6,7-dihydroxy-isochroman (1) indicates that this protocol can be used to synthesize oxygenated analogues of benzyl-tetrahydroisoquinoline alkaloids, such as demethyl-coclaurine (2). This methodology could be applied as a general procedure for the synthesis of hydroxy-isochromans. (literal)
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