An efficient bidirectional approach to the C2-symmetric stereoisomers of the bistetrahydrofuran core of the acetogenins

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4247-4251

  Marshall, James A ^a   Hinkle, Kevin W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030037718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9603789     Document Type: Article

References (15)

1. Cf. Zhao, G.-X.; Gu, Z.-M.; Zeng, L.; Chao, J.-F.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1995, 51, 7149 and references cited therein. Wu, Y.-C.; Chang, F.-R.; Chen, K.-S.; Liang, S.-C.; Lee, M.-R. Heterocycles 1994, 38, 1475. Hoppe, R.; Scharf, H.-D. Synthesis 1996, 1447.
2. Cf. Zhao, G.-X.; Gu, Z.-M.; Zeng, L.; Chao, J.-F.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1995, 51, 7149 and references cited therein. Wu, Y.-C.; Chang, F.-R.; Chen, K.-S.; Liang, S.-C.; Lee, M.-R. Heterocycles 1994, 38, 1475. Hoppe, R.; Scharf, H.-D. Synthesis 1996, 1447.
3. Cf. Zhao, G.-X.; Gu, Z.-M.; Zeng, L.; Chao, J.-F.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1995, 51, 7149 and references cited therein. Wu, Y.-C.; Chang, F.-R.; Chen, K.-S.; Liang, S.-C.; Lee, M.-R. Heterocycles 1994, 38, 1475. Hoppe, R.; Scharf, H.-D. Synthesis 1996, 1447.
4. Cf. Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. J Org. Chem. 1995, 60, 4419. Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981. Sinha, S. C.; Sinha-Bagehi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257.
5. Cf. Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. J Org. Chem. 1995, 60, 4419. Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981. Sinha, S. C.; Sinha-Bagehi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257.
6. Cf. Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. J Org. Chem. 1995, 60, 4419. Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981. Sinha, S. C.; Sinha-Bagehi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257.
7. Cf. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
8. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
9. For a recent example of such a cyclization, see: Koert, U.; Wagner, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1873.
10. Saito, S.; Narahara, O.; Ishikawa, T.; Asahara, M.; Moriwake, T. Gawronski, J.; Kazmierczak, F. J. Org. Chem. 1993, 58, 6292. Dialdehyde 3.3 was of >90% ee based on comparison of the optical rotation of the precursor 3.1 with the literature value.
11. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647. The stannanes employed in these studies were of 90-95% ee according to comparison of optical rotations to those of samples whose ee's were determined independently.
12. 3-promoted additions to unbranched aldehydes typically yield ca. 95:5 mixtures of syn and anti adducts.
13. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
14. For an analysis of these spectra, see the supporting information.
15. 3. For a summary of experimental protocols, see: Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960.