LETTER
Asymmetric Synthesis of 1-epi-(+)-MK7607
3509
(13) Block, O. Dissertation; University of Wuppertal: Germany,
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References and Notes
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H. Liebigs Ann. Chem. 1992, 637. (b) Chupak, L.;
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46, 6257.
(19) Analytical Data of 3.
Rf = 0.15 (EtOAc–MeOH = 6:1); [a]D22 232.7 (c 1.25, H2O).
1H NMR (300 MHz, D2O): d = 3.49 (dd, J = 10.9, 4.2 Hz, 1
H), 3.59 (dd, J = 10.9, 7.4 Hz, 1 H), 4.03 (m, 1 H), 4.09 (m,
2 H, CH2OH), 4.16 (d, J = 4.2 Hz, 1 H), 5.66 (m, 1 H,
C=CH) ppm. 13C NMR (75 MHz, D2O): d = 61.8 (CH2OH),
66.5, 70.7, 71.7, 72.3 (CHOH), 126.9 (C=CH), 137.5
(C=CH). MS (EI, 70 eV): m/z (%) = 140 (7), 122 (10), 116
(47), 111 (28), 99 (17), 98 (100), 97 (21), 83 (11), 81 (13),
71 (11), 72 (14), 69 (27), 55 (15). HRMS: m/z calcd for
C7H12O5 – 2H2O [M+ – 2H2O]: 140.04734; found:
140.04735.
Synlett 2006, No. 20, 3507–3509 © Thieme Stuttgart · New York