Stereocontrolled synthesis of (+)-acuminolide and determination of its absolute configuration

Chemistry Letters

Volumn , Issue 11, 1999, Pages 1247-1248

  Furuichi, Noriyuki ^a   Kato, Mariko ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033235116     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.1247     Document Type: Article

References (11)

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2. P. A. Zoretic, H. Fang, A. A. Ribeiro, and G. Dubay, J. Org. Chem., 63, 1156 (1998).
3. T. Hata, K. Tanaka, and S. Katsumura, Tetrahedron Lett., 40, 1731 (1999).
4. J. D. White, R. W. Skeean, and G. L. Trammell, J. Org. Chem., 50, 1939 (1985).
5. 3: C, 72.91; H, 10.89%.
6. K. Shishido, Y. Tokunaga, N. Omachi, K. Hiroya, and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1999, 2481.
7. 2, PCC, PDC, and actived DMSO gave poor yield of the corresponding ketone.
8. + 448.3009.
9. 1H NMR.
10. Treatment of the crude alcohol which was obtained from 7 by L-Selectride® reduction, with p-TsCl in pyridine gave the same result as that of the acid treatment. These results clearly show that the reduction stereoselectively proceeded to exclusively produce the (12R)-stereoisomer.
11. Although we obtained the most stable conformation of the compound 7 by means of molecular mechanics calculation, we could not draw the clear conclusion to understand the stereoselectivity of the reductions.