syn-Oxidative polycyclizations of hydroxypolyenes: Highly stereoselective and potentially biomimetic syntheses of all-trans- polytetrahydrofurans

Journal of the American Chemical Society

Volumn 119, Issue 26, 1997, Pages 6022-6028

  Towne, Timothy B ^a   McDonald, Frank E ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; GONIOCIN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CYCLIZATION; DRUG SYNTHESIS; OXIDATION; STEREOCHEMISTRY;

EID: 0030847206     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962837t     Document Type: Article

References (56)

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2. For recent reviews, see: (a) Koert, U. Synthesis 1995, 115. (b) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. (c) Figadere, B. Acc. Chem. Res. 1995, 28, 359. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275.
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51. Kishi first showed that E-trisubstituted alkenyl alcohols analogous to 24 afford trans-tetrahydrofuranyl alcohols via vanadium-catalyzed epoxidation/anti-cyclization. (a) Fukuyama, T.; Vranesic, B.; Negri, P.; Kishi, Y. Tetrahedron Lett. 1978, 31, 2741. (b) Wuts, P. G. M.; D'Costa, R.; Butler, W. J. Org. Chem. 1984, 49, 2582. (c) Reference 12d.
52. Kishi first showed that E-trisubstituted alkenyl alcohols analogous to 24 afford trans-tetrahydrofuranyl alcohols via vanadium-catalyzed epoxidation/anti-cyclization. (a) Fukuyama, T.; Vranesic, B.; Negri, P.; Kishi, Y. Tetrahedron Lett. 1978, 31, 2741. (b) Wuts, P. G. M.; D'Costa, R.; Butler, W. J. Org. Chem. 1984, 49, 2582. (c) Reference 12d.
53. Kishi first showed that E-trisubstituted alkenyl alcohols analogous to 24 afford trans-tetrahydrofuranyl alcohols via vanadium-catalyzed epoxidation/anti-cyclization. (a) Fukuyama, T.; Vranesic, B.; Negri, P.; Kishi, Y. Tetrahedron Lett. 1978, 31, 2741. (b) Wuts, P. G. M.; D'Costa, R.; Butler, W. J. Org. Chem. 1984, 49, 2582. (c) Reference 12d.
54. 2O afforded 47 and 49 as single diastereomers.
55. We have noticed that the diastereomer ratios obtained with the dichloroacetylperrhenate reagents varied slightly between experiments, suggesting that there may be a concentration dependence of acid on the stereoselectivity of syn-oxidative cyclization reactions.
56. After considerable difficulty we obtained small amounts of the Mosher esters from reaction of 49 with (R)- and (S)-MTPA (Rieser, M. J.; Hui, Y.-h.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10203); however, the chemical shift differences at H14 for each Mosher ester were less than 0.01 ppm. A similarly minute difference in chemical shift was observed in goniocin (ref 3a).