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21
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33645036279
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22
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44349187061
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-1.
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-1.
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23
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44349107369
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3).
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3).
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25
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33845554880
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(b) Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378.
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Sharpless, K.B.4
Viti, S.M.5
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26
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44349112677
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3): δ = 25.1, 33.9, 37.4, 38.5, 61.7, 72.0, 114.9, 138.9.
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3): δ = 25.1, 33.9, 37.4, 38.5, 61.7, 72.0, 114.9, 138.9.
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27
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44349137185
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-1.
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-1.
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28
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0043194171
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Chaterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
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Chaterjee, A.K.1
Choi, T.-L.2
Sanders, D.P.3
Grubbs, R.H.4
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44349091828
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-1.
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-1.
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30
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1542421110
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Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1 1996, 967.
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Banwell, M.G.1
Bui, C.T.2
Pham, H.T.T.3
Simpson, G.W.4
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31
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44349145406
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Compound 8 (trans isomer, α]D 20 -43.1 (c, 1, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 0.04 (s, 6 H, 2 x Me, 0.88 (s, 9 H, 3 x Me, 1.24-1.48 (m, 2 H, 1.51-1.70 (m, 5 H, 1.90-2.02 (m, 1 H, 2.41 (dd, J, 5.5, 14.7 Hz, 1 H, 2.59 (dd, J, 8.3, 14.7 Hz, 1 H, 3.60-3.67 (m, 2 H, 3.67 (s, 3 H, 3.89-3.94 (m, 1 H, 4.10-4.16 (m, 1 H, 13C NMR (75 MHz, CDCl3, δ, 5.0 (2 x C, 18.6, 18.8, 26.3 (3 x C, 29.9, 30.4, 35.9, 39.9, 51.9, 60.2, 67.9, 69.1, 172.3. IR: 2928, 2856, 1746, 1463, 1361, 1288, 1256, 1206, 1159, 1092, 1050, 836, 776. cis-Isomer: [α]D20 -18.2 (c, 1, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 0.03 (s, 6 H, 2 x Me, 0.88 (s, 9 H, 3 x Me, 1.18-1.25 (m, 2 H, 1.46-1.73 (m, 5 H, 1.79-1.84 (m, 1 H, 2.38 (dd, J, 5.8, 14.7 Hz, 1 H, 2.53 dd, J, 7.5, 14.7 Hz
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-1.
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-
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32
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44349115322
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-1.
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-1.
-
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34
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0001424632
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Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731.
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(1996)
J. Org. Chem
, vol.61
, pp. 2731
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Marton, D.1
Stivanello, D.2
Tagliavini, G.3
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36
-
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44349172650
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trans-1: [α]D20 -11.3 (c, 0.25, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 1.35-1.39 (m, 2 H, 1.62-1.91 (m, 4 H, 1.90 (dd, J, 1.5, 6.8 Hz, 3 H, 2.44 (dd, J, 5.8, 14.9 Hz, 1 H, 2.62 (dd, J, 6.6, 15.2 Hz, 1 H, 2.66 (dd, J, 8.1, 14.9 Hz, 1 H, 2.88 (dd, J, 6.6, 15.2 Hz, 1 H, 3.66 (s, 3 H, 4.17-4.30 (m, 2 H, 6.13 (dq, J, 1.5, 15.6 Hz, 1 H, 6.85 (dq, J, 6.8, 15.6 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 18.6, 23.5, 31.2, 31.5, 41.9, 47.0, 51.9, 74.8, 75.0, 132.7, 143.6, 172.0, 198.8. IR: 2938, 2860, 1739, 1668, 1626, 1433, 1373, 1352, 1289, 1200, 1066 cm-1. HRMS (CI, m/z [M, H, calcd for C13H21O4: 241.1440; found: 241.1436. Chiral HPLC: ChiralPak AD, hexane-i-PrOH (90:10, λ, 225 nm, flow rate: 0.5 mL/min, tR, 22.4 min m
-
R = 22.4 min (minor) and 25.5 min (major).
-
-
-
-
37
-
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44349130092
-
-
-1.
-
-1.
-
-
-
-
38
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44349126430
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cis-1: [α]D20 +10.0 (c, 0.94, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 1.12-1.27 (m, 3 H, 1.49-1.66 (m, 3 H, 1.89 (dd, J, 1.5, 6.9 Hz, 3 H, 2.37 (dd, J, 5.6, 14.9 Hz, 1 H, 2.46-2.53 (m, 2 H, 2.80 (dd, J, 6.8, 15.3 Hz, 1 H, 3.65 (s, 3 H, 3.69-3.86 (m, 2 H, 6.13 (dq, J, 1.5, 15.6 Hz, 1 H, 6.84 (dq, J, 6.9, 15.6 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 18.6, 23.5, 31.2, 31.5, 42.9, 47.0, 51.8, 74.8, 75.0, 132.7, 143.6, 172.0, 198.8. IR: 2937, 2857, 1740, 1668, 1627, 1434, 1375, 1350, 1289, 1198, 1066 cm-1. HRMS (CI, m/z [M, H, calcd for C13H21O 4: 241.1440; found: 241.1437. Chiral HPLC: ChiralPak AD, hexane-i-PrOH (90:10, λ, 225 nm, flow rate: 0.5 mL/min, tR, 18.2 min (minor) and 19.9 min major
-
R = 18.2 min (minor) and 19.9 min (major).
-
-
-
-
39
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41049099493
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After submission of this manuscript, a similar approach was reported in the literature, see
-
After submission of this manuscript, a similar approach was reported in the literature, see: Bates, R. W.; Palani, K. Terahedron Lett. 2008, 49, 2832.
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(2008)
Terahedron Lett
, vol.49
, pp. 2832
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Bates, R.W.1
Palani, K.2
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