4.2 Article

SYNTHESIS OF 8-HYDROXYISOCHROMENES AND 8-HYDROXYISOCOUMARINS FROM 3-ETHOXYCYCLOHEX-2-EN-1-ONE

期刊

HETEROCYCLES
卷 84, 期 2, 页码 983-1012

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-11-S(P)73

关键词

8-Hydroxyisochromene; 8-Hydroxyisocoumarin; DDQ; Oopolactone; Pyran Formation

资金

  1. National Science Foundation [CHE-0506486]

向作者/读者索取更多资源

Two strategies were developed to prepare 8-hydroxyisocoumarins from substituted 3-ethoxycyclohex-2-en-1-ones. The key reactions in the first strategy were the cyclization of a 2-hydroxymethy1-3-ethynyl-cyclohex-2-en-1-one, followed by the aromatization of the resulting cyclohexenone-pyran intermediate. The second approach featured the reaction of 2-hydroxymethy1-3-vinyl-cyclohex-2-en-1-ones with DDQ to directly produce isocoumarins. This new two-step sequence was used to prepare oospolactone in 57% overall yield.

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