First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2703-2706

  Kim, Sanghee ^a   Lee, Jaekwang ^a   Lee, Taeho ^a   Park, Hyeung Geun ^a   Kim, Deukjoon ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID DERIVATIVE; ANTINEOPLASTIC AGENT; ANTOFINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CANCER CELL; CATALYSIS; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ALKALOIDS; ALKYLATION; CATALYSIS; CYCLIZATION; INDOLES; PHENANTHROLINES; PYRROLIDINES; STEREOISOMERISM;

EID: 0141631522     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0349007     Document Type: Article

References (47)

1. Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Academic Press: New York, 1987; pp 55-132.
2. Suffness, M.; Cordell, G. A. In The Alkaloids, Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 25, pp 3-355.
3. Stærk, D.; Lykkeberg, A. K.; Christensen, J.; Budnik, B. A.; Abe, F.; Jaroszewski, J. W. J. Nat. Prod. 2002, 65, 1299-1302 and references therein.
4. For a good review with citations to recent work, see: (a) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1999, 55, 2659-2670. (b) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082-12089. (c) Pearson, W. H.; Walavalkar, R. Tetrahedron 1994, 50, 12293-12304.
5. For a good review with citations to recent work, see: (a) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1999, 55, 2659-2670. (b) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082-12089. (c) Pearson, W. H.; Walavalkar, R. Tetrahedron 1994, 50, 12293-12304.
6. For a good review with citations to recent work, see: (a) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1999, 55, 2659-2670. (b) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082-12089. (c) Pearson, W. H.; Walavalkar, R. Tetrahedron 1994, 50, 12293-12304.
7. Lee, S. K.; Nam, K.-A.; Heo, Y.-H. Plant Med. 2003, 69, 21-25.
8. For a synthesis of racemic antofine, see: (a) Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360. (b) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516. (c) Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962. (d) Iwao, M.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron Lett. 1981, 22, 2349-2352. (e) Bhakuni, D. S.; Gupta, P. K. Indian J. Chem., Sect. B 1982, 21B, 393-395. See also refs 4a and 4b.
9. For a synthesis of racemic antofine, see: (a) Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360. (b) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516. (c) Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962. (d) Iwao, M.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron Lett. 1981, 22, 2349-2352. (e) Bhakuni, D. S.; Gupta, P. K. Indian J. Chem., Sect. B 1982, 21B, 393-395. See also refs 4a and 4b.
10. For a synthesis of racemic antofine, see: (a) Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360. (b) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516. (c) Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962. (d) Iwao, M.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron Lett. 1981, 22, 2349-2352. (e) Bhakuni, D. S.; Gupta, P. K. Indian J. Chem., Sect. B 1982, 21B, 393-395. See also refs 4a and 4b.
11. For a synthesis of racemic antofine, see: (a) Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360. (b) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516. (c) Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962. (d) Iwao, M.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron Lett. 1981, 22, 2349-2352. (e) Bhakuni, D. S.; Gupta, P. K. Indian J. Chem., Sect. B 1982, 21B, 393-395. See also refs 4a and 4b.
12. For a synthesis of racemic antofine, see: (a) Govindachari, T. R.; Ragade, I. S.; Viswanathan, N. J. Chem. Soc. 1962, 1357-1360. (b) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503-2516. (c) Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962. (d) Iwao, M.; Watanabe, M.; De Silva, S. O.; Snieckus, V. Tetrahedron Lett. 1981, 22, 2349-2352. (e) Bhakuni, D. S.; Gupta, P. K. Indian J. Chem., Sect. B 1982, 21B, 393-395. See also refs 4a and 4b.
13. For a synthesis of the antipodal isomer of antofine, see: (a) Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1976, 59, 2201-2212. (b) Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1973, 56, 2882-2884.
14. For a synthesis of the antipodal isomer of antofine, see: (a) Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1976, 59, 2201-2212. (b) Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1973, 56, 2882-2884.
15. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
16. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
17. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
18. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
19. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
20. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
21. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
22. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
23. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
24. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
25. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A. ; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772. (k) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774-7780.
26. Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661-3666.
27. This compound appeared to be sensitive to silica gel chromatography. It was very important to minimize the residency time of this compound on the chromatography column to obtain this product in high yield.
28. Williams, R. M. Synthesis of Optically Active α-Amino Acids. Vol. 7 of Organic Chemistry Series; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, UK, 1989.
29. (a) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
30. (b) Chakraborty, T. K.; Ghosh, A. Tetrahedron Lett. 2002, 43, 9691-9693 and references therein.
31. For a good review with citations, see: (a) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036-3038. (b) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409. (c) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-15. (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
32. For a good review with citations, see: (a) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036-3038. (b) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409. (c) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-15. (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
33. For a good review with citations, see: (a) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036-3038. (b) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409. (c) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-15. (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
34. For a good review with citations, see: (a) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036-3038. (b) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409. (c) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-15. (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
35. For the previous asymmetric phase transfer alkylation involving bulky electrophiles, see ref 13a and: Lygo, B.; Andrews, B. I.; Crosby, J.; Peterson J. A. Tetrahedron Lett. 2002, 43, 8015-8018.
36. The absolute configuration of 12 was reconfirmed by transformation to the authentic natural compound (-)-1. The enantiomeric excess of 12 was determined by chiral stationary phase HPLC analysis (CHIRALCEL OD-H, hexane/2-propanol (9:1, v/v), flow rate 0.5 mL/min, retention time 25.52 min (S)-isomer and 30.33 min (R)-isomer, detected at 254 nm).
37. Albeck, A.; Persky, R. J. Org. Chem. 1994, 59, 653-657.
38. Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 566-574.
39. (a) Schwab, P.; Grubbs, R. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
40. (b) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
41. Nordlander, J. E.; Njoroge, F. G. J. Org. Chem. 1987, 52, 1627-1630.
42. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.
43. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.
44. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.
45. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.
46. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.
47. The optical rotation values of natural antofine range from -32° to -165°. see: (a) Cavé, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I. R. C.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Aust. J. Chem. 1989, 42, 2243-2263. (b) Baumgartner, B.; Erdelmeier, C. A. J.; Wright, A. D.; Rali, T.; Sticher, O. Phytochemistry 1990, 29, 3327-3330. (c) Li, X.; Peng, J.; Onda, M. Heterocycles 1989, 29, 1797-1808. (d) Herbert, R. B.; Moody, C. J. Phytochemistry 1972, 11, 1184-1184. (e) Capo, M.; Saa, J. M. J. Nat. Prod. 1989, 52, 389-390. (f) Wiegrebe, W.; Faber, L.; Brockmann, H., Jr.; Budzikiewicz, H. ; Krueger, U. Liebigs Ann. Chem. 1969, 721, 154-162. See also refs 3 and 7.