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Synthesis of (1S,5S)-4,5-Dihydro-1,5-epoxy-1H-2-benzoxocin-6(3H)-one from (S)-Malic Acid Derivatives

✍ Scribed by Wünsch, Bernhard ;Diekmann, Heike

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
997 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

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‐phenyl substituent with the electrophilic groups in position 4 of 8a–e in a Parham cyclization across the 1,3‐dioxane ring failed. The synthesis of the tricyclic title ketone 5a succeeded, however, by addition of the lithiated benzaldehyde acetal 7c to the protected α‐hydroxylactone 10b and subsequent treatment of the intermediate ketone 23 with acid. The acid hydrolysis of the alcohol 26, which was obtained by addition of 7c to the protected dihydroxy aldehyde 25b, followed by oxidation of the resulting alcohols 27a and b represent a second possibility for the preparation of the tricyclic ketone 5a.

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