Glycosylated indolocarbazole synthesis

US7038043B1 · kind B1 · utility

Assignee

• Yale University · US

Inventors

• John L. Wood · Hamden, US
• Brian M. Stoltz · San Marino, US
• Hans-Jürgen Dietrich · Frankfurt, DE
• Derek Pflum · Northville, US

Key dates

• Filing date: Jan 13, 2000
• Grant date: May 2, 2006
• Expiry date: Jan 13, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C45/68
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Indolocarbazoles are furanosylated (e.g., 7) with acetals (e.g., 8) or their open chain congeners (e.g., 9) under conditions known to promote acetal exchange or formation, such as protic or Lewis acids. Furanosylated indolocarbazoles (e.g., 10) are also prepared via ring contraction of pyranosylated indolocarbazoles (e.g., 11) under conditions know to effect oxidation and benzylic acid type rearrangements, and pyranosylated indolocarbazoles (e.g., 11) are prepared via ring expansion of the furanosylated congeners (e.g., 10)