Synthesis of a 2-aminohexahydrobenzoxazole analogue related to trehazolin

Article abstract of DOI:10.1021/jo00124a023

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.