gem-Dihalocyclopropanes as building blocks in natural-product synthesis: Enantioselective total syntheses of ent-erythramine and 3-epi-erythramine

Chemistry - An Asian Journal

Volumn 2, Issue 9, 2007, Pages 1127-1136

  Stanislawski, Pauline C ^a   Willis, Anthony C ^a   Banwell, Martin G ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

Alkaloids; Cyclopropanes; Radical reactions; Spirocyclization; Total synthesis

Indexed keywords

1,3 BENZODIOXOLE DERIVATIVE; BIOLOGICAL PRODUCT; CYCLOPROPANE DERIVATIVE; ERYTHRAMINE; ISOQUINOLINE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

BENZODIOXOLES; BIOLOGICAL PRODUCTS; CHROMATOGRAPHY, LIQUID; CYCLOPROPANES; ISOQUINOLINES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NITROGEN; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 34548559498     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700155     Document Type: Article

References (39)

1. For reviews and useful points of entry into the relevant literature, see: a) S. F. Dyke, S. N. Quessy in The Alkaloids, Vol. 18 (Ed: R. G. A. Rodrigo), Academic Press, New York, 1981, pp. 1-98;
2. b) A. S. Chawla, V. K. Kapoor in The Alkaloids: Chemical and Biological Perspectives, Vol. 9 (Ed.: S. W. Pelletier), Elsevier Science Ltd., Oxford, 1995, pp. 86-153;
3. c) Y. Tsuda, T. Sano in The Alkaloids, Vol. 48 (Ed.: G. A. Cordell), Academic Press, San Diego, 1996, pp. 249-337;
4. d) H. Tanaka, T. Tanaka, H. Etoh, S. Goto, Y. Terada, Heterocycles 1999, 51, 2759.
5. R. García-Mateos, M. Soto-Hernandez, D. Kelly, Biochem. Syst. Ecol. 1998, 26, 545.
6. For a comprehensive listing of synthetic studies reported up until early 2003, see: a) H. I. Lee, M. P. Cassidy, P. Rashatasakhon, A. Padwa, Org. Lett. 2003, 5, 5067; for studies reported between 2003 and early 2006, see:
7. b) P. C. Stanislawski, A. C. Willis, M. G. Banwell, Org. Lett. 2006, 8, 2143; for very recent studies, see:
8. c) S. Gao, Y. Q. Tu, X. Hu, S. Wang, R. Hua, Y. Jiang, Y. Zhao, X. Fan, S. Zhang, Org. Lett. 2006, 8, 2373;
9. d) I. Osante, M. N. Abdullah, S. Arrasate, N. Sotomayor, E. Lete, ARKIVOC 2007, iv, 206.
10. a) M. G. Banwell, R. W. Gable, S. C. Peters, J. R. Phyland, J. Chem. Soc. Chem. Commun. 1995, 1395;
11. b) M. Banwell, A. Edwards, J. Harvey, D. Hockless, A. Willis, J. Chem. Soc. Perkin Trans. 1 2000, 2175;
12. c) M. G. Banwell, J. E. Harvey, D. C. R. Hockless, A. W. Wu, J. Org. Chem. 2000, 65, 4241;
13. d) M. G. Banwell, W. Ebenbeck, A. J. Edwards, J. Chem. Soc. Perkin Trans. 1 2001, 114;
14. e) M. G. Banwell, J. E. Harvey, K. A. Jolliffe, J. Chem. Soc. Perkin Trans. 1 2001, 2002;
15. f) M. G. Banwell, A. J. Edwards, K. A. Jolliffe, J. A. Smith, E. Hamel, P. Verdier-Pinard, Org. Biomol. Chem. 2003, 1, 296;
16. g) R. M. Taylor, Aust. J. Chem. 2003, 56, 631;
17. h) M. G. Banwell, M. O. Sydnes, Aust. J. Chem. 2004, 57, 537;
18. i) see reference [3b];
19. j) J. S. Foot, A. T. Phillis, P. P. Sharp, A. C. Willis, M. G. Banwell, Tetrahedron Lett. 2006, 47, 6817;
20. k) M. G. Banwell, F. Vogt, A. W. Wu, Aust. J. Chem. 2006, 59, 415;
21. l) M. G. Banwell, A. T. Phillis, A. C. Willis, Org. Lett. 2006, 8, 5341; for a review of certain aspects of our work in this area, see:
22. m) M. G. Banwell, D. A. S. Beck, P. C. Stanislawski, M. O. Sydnes, R. M. Taylor, Curr. Org. Chem. 2005, 9, 1589.
23. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
24. M. Banwell, D. Hockless, B. Jarrott, B. Kelly, A. Knill, R. Longmore, G. Simpson, J. Chem. Soc. Perkin Trans. 1 2000, 3555.
25. a) L. A. Paquette, Z. Gao, Z. Ni, G. F. Smith, J. Am. Chem. Soc. 1998, 120, 2543;
26. b) L. A. Paquette, M. J. Earle, G. F. Smith, Org. Synth. 1996, 73, 36.
27. a) M. Makosza, M. Wawrzyniewicz, Tetrahedron Lett. 1969, 10, 4659; for a discussion of the methods available for the generation of dihalocarbenes, see:
28. b) M. G. Banwell, M. E. Reum in Advances in Strain in Organic Chemistry, Vol. 1 (Ed.: B. Halton), JAI Press, London, 1991, p. 19.
29. L. Xu, U. H. Brinker in Synthetic Organic Sonochemistry (Ed.: J.-L. Luche), Plenum Press, New York, 1998, p. 344.
30. R. K. Crossland, K. L. Servis, J. Org. Chem. 1970, 35, 3195.
31. H. Kunz, C. Unverzagt, Angew. Chem. 1984, 96, 426;
32. Angew. Chem. Int. Ed. Engl. 1984, 23, 436.
33. K. Folkers, F. Koniuszy, J. Am. Chem. Soc. 1939, 61, 1232.
34. R. B. Boar, D. A. Widdowson, J. Chem. Soc. B 1970, 1591.
35. a) M. E. Jung, J. A. Berliner, D. Angst, D. Yue, L. Koroniak, A. D. Watson, R. Li, Org. Lett. 2005, 7, 3933;
36. b) D. R. Deardorff, C. Q. Windham, C. L. Craney, Org. Synth. 1996, 73, 25.
37. Z. Otwinowski, W. Minor in Methods in Enzymology, Vol. 276: Macromolecular Crystallography, Part A (Eds.: C. W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
38. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
39. P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Crystallogr. 2003, 36, 1487.