First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans: Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1310-1316

  Yoshida, Shin Ichi ^a   Ogiku, Tsuyoshi ^a   Ohmizu, Hiroshi ^a   Iwasaki, Tameo ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001392802     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961733y     Document Type: Article

References (42)

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2. Reviews: (a) Chemistry of lignans; Rao, C. B. S., Ed.; Andhra Univ. Press: India, 1978. (b) Lignans; Ayres, D. C.; Loike, J. D., Ed.; Cambridge University Press: New York, 1990. (c) Ward, R. S. Chem. Soc. Rev. 1982, 11, 75.
3. Reviews: (a) Chemistry of lignans; Rao, C. B. S., Ed.; Andhra Univ. Press: India, 1978. (b) Lignans; Ayres, D. C.; Loike, J. D., Ed.; Cambridge University Press: New York, 1990. (c) Ward, R. S. Chem. Soc. Rev. 1982, 11, 75.
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31. The stereochemistry of 8 and 9 was unambiguously confirmed by X-ray crystallographic analysis of 21 and 3a.
32. Addition of veratraldehyde to a mixture of the acid anhydride and LDA in THF at -50°C did not give the coupling products at all.
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34. In order to improve the selectivity, we tried to exchange the countercation of the enolate of acid anhydride 8 from Li to Mg, Sn or Zn by addition of the metal salts. But, the lithium enolate of 8 was so unstable that the enolate of these metals could not be generated.
35. To the best of our knowledge, it has not been reported that a Potassium countercation of an enolate enhances the stereoselectivity inhibits aldol reaction. The high syn-selectivity observed in the use of KHMDS in the present work would be elucidated by higher stability of the twist-boat transition structure leading to the syn-isomer than that of the chair transition structure leading to the anti-isomer.
36. 1H NMR data of 21, 22, 25, and 26 were summarized in supporting information.
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38. The isomerization of the bislactone under the acidic conditions was reported by Snieckus et al. See ref 7.
39. 2 = 3,4-methylenedioxy) was determined by X-ray crystallographic analyses.
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41. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK
42. Pelter, A.; Ward, R. S.; Rao, E. V.; Sastry, K. V. Tetrahedron 1976, 32, 2783.