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2,6-Epoxy-3-benzoxocin-4-ol-Derivate durch zweifache intramolekulare Halbacetalbildung

✍ Scribed by Wünsch, Bernhard ;Bauschke, Gerd

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 636 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199119910110

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✦ Synopsis

2,6‐Epoxy‐3‐benzoxocin‐4‐ol Derivatives by Double Intramolecular Formation of Hemiacetals

With dilute HCl the hydroxydialdehyde derivatives 10a‐c are cyclised to give the tricyclic hemiaccetals 6a–c. This double intramolecular formation of hemiacetals succeeds well, if R in 10 is not hydrogen; if R = H an equilibrium betwen 5a and 6a is observed. The ^1^H‐NMR data of 6 and 17 support the chair conformation of the 1,3‐dioxane ring bearing an equatorial substituent (OH, OAc) in position 4.

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## Abstract The homochiral 1,3‐dioxanes 8a–e with a 2‐bromophenyl substituent in position 2 and an electrophilic group in position 4 were stereo‐ and regioselectively prepared from the (__S__)‐malic acid derivatives 6a, 6b, 11, and 14. Attempts to prepare the tricycles 5a–c by connecting the 2‐phen