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1
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1542716587
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Zeneca Fellow 1994-1997
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Zeneca Fellow 1994-1997.
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2
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0017744727
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(e) Sinaÿ, P., In Bio-organic Heterocycles, 1986; Synthesis, Mechanisms and Bioactivity; Van der Plas, H.; Simonyi, M.; Aiderweireidt, F. C.; Lepoivre, J. A., Eds.; Elsevier: Amsterdam, 1986, pp 59-74.
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(a) Kende, A. S.; Mendoza, J. S.; Fujii, Y. Tetrahedron 1993, 49, 8015.
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(f) Markó, I. E.; Bailey, M.; Murphy, F.; Declercq, J-P.; Tinant, B.; Feneau-Dupont, J.; Krief, A.; Dumont, W. Synlett 1995, 123.
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For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
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Asao, N.2
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For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
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For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
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Tarbet, K.H.2
Geraci, L.S.3
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For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
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For a review on the oxidation of carbon-halogen bonds, see: (a) Kilenyi, S. N. In Trost, B. M.; Fleming, I., Eds.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991; Vol. 7, p 653. Dave, P.; Byun, H-P.; Engel, R. Synth. Commun. 1986, 16, 1343.
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This sequence could involve inter-alia, the Pummerer rearrangement of sulfide 12 into an aldehyde followed by addition of MeMgI and oxidation of the resulting alcohol to the methyl ketone
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This sequence could involve inter-alia, the Pummerer rearrangement of sulfide 12 into an aldehyde followed by addition of MeMgI and oxidation of the resulting alcohol to the methyl ketone.
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Olefin 18 was initially transformed into the α-diol 21 in 67% yield using the Upjohn catalytic dihydroxylation protocol: Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1987, 1973. It is interesting to note that osmylation proceeds from the least hindered face of the dihydropyran substrate (Scheme 6). Benzoylation of 21, using p-bromobenzoyl chloride (pBBCl) in the presence of catalytic quantities of 4-dimethylamino pyridine, resulted in the preferential formation of the monobenzoylated material 22 accompanied by minor amounts of the bis-benzoylated compound 20. Although crystalline, 22 proved unsuitable for X-Ray analysis, the minor bis-benzoyl derivative 20 gave good quality X-Ray crystals.
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(1987)
Tetrahedron Lett.
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Van Rheenen, V.1
Kelly, R.C.2
Cha, D.Y.3
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