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  • Title: Structure of a dihydrooxazole oxa-bridged octalin.
    Author: Ostrander RL, Kallmerten J, Rossano LT.
    Journal: Acta Crystallogr C; 1991 Nov 15; 47 ( Pt 11)():2410-3. PubMed ID: 1805868.
    Abstract:
    C26H41NO7, Mr = 479.61, triclinic, P1, a = 11.894 (4), b = 12.360 (2), c = 9.969 (2) A, alpha = 106.11 (2), beta = 100.68 (2), gamma = 99.02 (2) degrees, V = 1349.5 (6) A3, Z = 2, Dx = 1.180 Mg m-3, Mo K alpha, lambda = 0.71069 A, mu = 0.079 mm-1, F(000) = 520, T = 296 K, R = 0.041, wR = 0.047 for 3196 observed unique reflections. A new approach to the total synthesis of the nargenicin macrolide system employing a [2,3] Wittig rearrangement to control the remote C16-C17 stereochemistry required characterization of a pivotal intermediate by X-ray single-crystal methods. The structure is characterized by the formation of strong intermolecular alcohol to dihydrooxazole-N hydrogen bonds, an essentially strain-free tricyclic oxa-bridged octalin nucleus, and low-energy conformations of the methoxymethyl ether side chains.
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