Synthesis of (+)-(15,16,19,20,23,24)-Aexepy-Uvaricin: A Bis(tetrahydrofuranyl) Annonaceous Acetogenin Analogue

Journal of the American Chemical Society

Volumn 113, Issue 24, 1991, Pages 9369-9371

  Hoye, Thomas R ^a   Hanson, Paul R ^a   Kovelesky, Albert C ^a   Ocain, Timothy D ^a   Zhuang, Zhiping ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000843364     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00024a053     Document Type: Article

References (28)

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10. The yield of intermediate bis-β-ketoester using the tert-butyl ester (55–60%) was higher than when methyl acetoacetate was used.7b,c
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16. Under the assumption that both the α- and ω-primary alcohols react at identical rates, in theory the use of 1.0 equiv of p-TsCl maximizes the yield of the monotosylate (to 50%) and 1.33 equiv leads to the formation of equivalent amounts of mono- and ditosylates (∼45% each).
17. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
18. See also: Morris, J.; Wishka, D. G. Tetrahedron Lett. 1986, 27, 803.
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20. To prepare 10 the potassium enolate anion derived (KHMDS, THF, 0 °C) from a mixture of (2R,4S)- and (2S,4S)-4-methyl-2-phenyl-sulfenyl-γ-butyrolactone13a was treated with (E)-l,9-diiodo-l-nonene (prepared from reaction of l-nonyn-9-ol with Ph3P, I2, and ImH at room temperature in MeCN/Et2O and then catechol-borane and iodine13b) and immediately brought to reflux for 2 h (protocol developed by E. A. Craig in our laboratories) to give a 70% yield of a 4:1 ratio of 10 and 2-epi-10.
21. Iwai, K.; Kosugi, H.; Uda, H.; Kawai, M. Bull. Chem. Soc. Jpn. 1977, 50, 242.
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25. We are indebted to Professors J. R. Cole and J. J. Hoffmann for providing natural uvaricin.
26. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991,113,4092.
27. Hui, Y.; Rupprecht, J. K.; Rieser, M. J.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hoye, T. R.; Hanson, P. R.; Zhuang, Z. Manuscript in preparation.
28. The C(35), C(36), and C(37) protons have identical chemical shifts in the 1/11, S-MTPA-l/R-MTPA-11, and R-MTPA-1/S-MTPA-H diastereomeric pairs, suggesting that those sites are sufficiently far removed from the C(15) Mosher ester attachment site to be unaffected.