[OH:1][C:2]12[CH2:9][CH2:8][C:5](C(O)=O)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.CC[N:15]([CH:19](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[OH:1][C:2]12[CH2:3][CH2:4][C:5]([NH:15][C:19](=[O:29])[O:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([CH2:6][CH2:7]1)[CH2:8][CH2:9]2To a solution of 4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid (10.4 g, 61.1 mmol) in dioxane (150 mL) was added DIEA (11.8 g, 91.5 mmol), diphenyl phosphoryl azide (25 g, 91.5 mmol) and benzyl alcohol (131 g, 1.22 mol). The mixture was stirred at 80° C. overnight. Then the reaction was concentrated under reduce pressure to remove dioxane and benzyl alcohol (100° C., 2 mm Hg). The residue was purified by silica gel column chromatography (5% methanol in DCM) to give the title product (15.4 g, 54 mmol, yield 91%). 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.30 (m, 5H), 5.03 (s. 2H), 4.55 (br s, 1H), 2.01-1.95 (m, 6H), 1.77-1.72 (m, 6H; MS (ESI) m/z 276.3 [M+H]+.
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