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8
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33748932590
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note
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(a) Material Safety Data Sheet: Moxidectin: Fort Dodge Animal Health.
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10
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33748924945
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Milbemycin class efflux pump inhibitors for treating microbial infections and cancer. WO 98-US20916 19981001, 1999 AN 1999:244572
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Chamberland, S.; Lee, M.; Lomovskaya, O. Milbemycin class efflux pump inhibitors for treating microbial infections and cancer. WO 98-US20916 19981001, 1999 AN 1999:244572.
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Chamberland, S.1
Lee, M.2
Lomovskaya, O.3
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Smith III, A.B.1
Schow, S.R.2
Bloom, J.D.3
Thompson, A.S.4
Winzenberg, K.N.5
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(b) Schow, S. R.; Bloom J. D.; Thompson, A. S.; Winzenberg, K. N.; Smith, A. B., III. J. Am. Chem. Soc. 1986, 108, 2662-2674.
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Smith III, A.B.5
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(g) Barrett, A. G. M.; Carr, R. A. E.; Attwood, S. V.; Richardson, G.; Walshe, N. D. A. J. Org. Chem. 1986, 51, 4840-4856.
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Walshe, N.D.A.5
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18
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(a) Yeater, C.; Street, S. D. A.; Kocienski, P.; Campbell, S. F. J. Chem. Soc., Chem. Commun. 1985, 1388-1389.
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Crimmins, M.T.1
Bankaitis-Davis, D.M.2
Hollis Jr., W.G.3
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22
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33748948821
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note
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3 could be prepared from an achiral starting material, see: ref 8d.
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23
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33748928858
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note
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We prepared phosphine oxide 3 by a slightly modified variant of the Smith route, see Supporting Information and ref 7b.
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24
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85077634689
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Barrett had previously shown that the C-19 carboxylate could be installed by a Mitsunobu reaction, see: ref 7g and Mitsunobu, O. Synthesis 1981, 1-28.
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(1981)
Synthesis
, pp. 1-28
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Mitsunobu, O.1
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25
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0000417893
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For examples of the asymmetric hydration of unsubstituted dienoates (e.g. 10 to 8), see: Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3(7), 1049-1052. Our study of the asymmetric hydration of substituted dienoates, will be published in due course.
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Org. Lett.
, vol.3
, Issue.7
, pp. 1049-1052
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Hunter, T.J.1
O'Doherty, G.A.2
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29
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14844356105
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Because most of the enantiomeric impurity in 7 is converted into the minor diastereomer ent-17b during the asymmetric dihydroxylation (7 to 17a/b), the major diastereomer diol 17a was isolated in essentially enantiomeric pure form. Consequently, the minor diastereomer I7b must be formed with lower enantiopurity. For other examples of this enantio-enriching phenomena, see: Ahmed, Md. M.; Berry, B. P.; Hunter, T. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745-748.
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Org. Lett.
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Ahmed, Md.M.1
Berry, B.P.2
Hunter, T.J.3
Tomcik, D.J.4
O'Doherty, G.A.5
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30
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33748938089
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note
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2/hexane solvent mixture was critically important to ensure high yields for the palladium catalyzed reduction. For instance, use of THF as solvent gave a 1: 1 mixture of double bond regioisomers.
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31
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0142214632
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(a) Nelson, S. G.; Bungard, C. J.; Wang, K. J. Am. Chem. Soc. 2003, 125, 13000-13001.
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Nelson, S.G.1
Bungard, C.J.2
Wang, K.3
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33
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33748928048
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note
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3 has been a source of disagreement. For an interesting discussion of this issue along with its resolution, see: ref 7 g.
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