First Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7586-7587

  Nishimata, Toyoki ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001092327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815249     Document Type: Article

References (36)

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26. Substrate 4a and 4b were synthesized by the same procedure as that previously reported.7 For experimental details, see Supporting Information.
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29. The ee value of 9 was determined by HPLC analysis (DAICEL CHIRALPAK AS, hexane/2-propanol 9/1).
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31. The ee of 11 was determined by HPLC (DAICEL CHIRALCEL OD) to be 70% ee. Probably, compound 6 was partially racemizcd by coordination of SnCU to the tosyl amide group.
32. When compound 16 was treated with 100 mol % of SnCl4 at -5 °C, unusual rearrangement products were obtained in 19% yield as a mixture of 17 and 18 along with 19. Table 2 SnCli-Promoted Carbonyl-ene Reaction of 16. However, this reaction was carried out using 10 mol % of SnCl4 to give 17 in 89% yield as a single product. By comparing with the spectral data of 17 and 18 and the spectra of the NOE experiments on them, the stereochemistry of these compounds could be determined. The stereochemistry of 11 was confirmed by a comparison with the above data.
33. A similar rearrangement has been reported: cf. Csuzdi, E.; Pallagi, I.; Jerkovich, G.; Sôlyom, S. Synlett 1994, 429.
34. 4f'5a'b compounds having the methyl group on nitrogen (in our case, tosyl group) were treated under the same reaction conditions to give only a-methoxylated product.
35. Kumar, H. M. S.; Reddy, B. V. S.; Mohanty, J. S.; Yadav, J. S. Tetrahedron Lett. 1997,38, 3619.
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