Journal of Organic Chemistry p. 6103 - 6109 (1995)
Update date:2022-09-26
Topics:
Miyazaki
Kobayashi
Shiozaki
Ando
Nakajima
Hanzawa
Haruyama
2-Aminohexahydrobenzoxazole analogue 1a, related to trehazolin (2) was synthesized using the Ferrier reaction as a key step. The structural elucidation of this compound by NMR analysis indicated that it is an inseparable mixture of three components (1a-c) which in turn stems from the propensity of la to partially undergo both transcyclization (1a → 1b) of the aminooxazoline between the hydroxy group at the C-1 position of aminocyclitol in the aglycon moiety and the hydroxy group at the C-2 position of D-glucose moiety and successive transformation (1b → 1c) of the D-glucose moiety from a pyranose to a furanose structure.
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