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For reviews of guianolide/pseudoguianolide syntheses see:. ApSimon J. (Ed), John Wiley & Sons, New York
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Pirrng M.C., Morehead Jr. A.T., and Young B.G. In: Goldsmith D. (Ed). The Total Synthesis of Natural Products Vol. 11 (2000), John Wiley & Sons, New York
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53749094941
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For a recent review on the synthesis of guianolides with a trans-lactone moiety see:
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For a recent review on the synthesis of guianolides with a trans-lactone moiety see:. Schall A., and Reiser O. Eur. J. Org. Chem. (2008) 2353-2364
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Schall, A.1
Reiser, O.2
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13
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11844306006
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Semi-syntheses of guianolides have been reported from photochemical rearrangement the naturally occurring terpene α-santonin:
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Semi-syntheses of guianolides have been reported from photochemical rearrangement the naturally occurring terpene α-santonin:. Zhang W., Luo S., Fang F., Chen Q., Hu H., Jia X., and Zhai H. J. Am. Chem. Soc. 127 (2005) 18-19
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33751350236
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Donaldson, W.A.5
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21
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58149521936
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note
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3) δ 0.81 (d, J = 9.0 Hz, 3H), 1.08 and 1.09 (2 × s, 9H total), 1.52-1.74 (m, 2H), 1.87-1.99 (m, 1H), 2.22-2.3.11 (m, 1H), 2.32-2.49 (m, 2H), 2.86-2.96 and 3.10-3.20 and 3.28-3.43 (m, 2H total), 4.06-4.19 and 4.32-4.39 (2 × m, 1H total), 5.24-5.50 (m, 2H), 5.81-5.92 (m, 1H), 7.35-7.49 (m, 6H), 7.65-7.76 (m, 4H).
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22
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0000353622
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A similar selective reduction has been reported:
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A similar selective reduction has been reported:. Davies H.M.L., and Doan B.D. J. Org. Chem. 63 (1998) 657-660
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(1998)
J. Org. Chem.
, vol.63
, pp. 657-660
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Davies, H.M.L.1
Doan, B.D.2
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23
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58149483412
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note
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+) m/z 450.2804).
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24
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58149512779
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note
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+) m/z 228.1576).
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27
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58149505614
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The crystallographic data for 21 has been deposited with the CCDC (CCDC 690098). This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.ccdc.cam.ac.uk.
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The crystallographic data for 21 has been deposited with the CCDC (CCDC 690098). This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.ccdc.cam.ac.uk.
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28
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58149512778
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note
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+) m/z 223.1334).
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