Fusicoccin ring system by [4 + 4] cycloaddition. 2. A model study

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 4007-4010

  Sieburth, Scott McN ^a   McGee Jr , Kevin F ^a   Al Tel, Taleb H ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Cycloaddition; Natural products; Photochemistry; Pyridones

Indexed keywords

FUSICOCCIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION;

EID: 0033591165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00671-1     Document Type: Article

References (39)

1. 1 Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
2. +-ATPase of the plasma membrane. See: Piotrowski, M.; Morsomme, P.; Boutry, M.; Oecking, C. J. Biol. Chem. 1998, 273, 30018-30023.
3. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
4. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
5. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
6. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
7. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
8. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
9. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
10. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
11. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
12. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
13. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
14. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
15. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
16. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
17. 3 For synthetic approaches to the fusicoccins and related 5-8-5 ring systems, see: Dauben, W. G.; Hart, D. J. J. Org. Chem. 1977, 42, 922-923. Begley, M. J.; Mellor, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1905-1912. Grayson, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Commun. 1984, 1695-1696. Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201-205. Mehta, G.; Krishnamurthy, N. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. Dauben, W. G.; Warshawsky, A. M. J. Org. Chem. 1990, 55, 3075-3087. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568-3572. Rigby, J. H.; McGuire, T.; Senanayake, C.; Khemani, K. J. Chem. Soc., Perkin Trans, 1 1994, 3449-3457. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716. Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 39-42. Harmata, M. Tetrahedron 1997, 53, 6235-6280. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Total synthesis of a biosynthetically related natural product, fusicocca-2,10(14)-diene, has recently been reported: Kato, N.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans, 1 1998, 2473-2474. see also reference 5.
18. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
19. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
20. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
21. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
22. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
23. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
24. 4 Ophiobolin C and the ceroplastols have been prepared by total synthesis: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737-2739. Paquette, L. A.; Wang, T.-Z.; Vo, N. H. J. Am. Chem. Soc. 1993,115, 1676-1683. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335-2338. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921-3932. Total synthesis of the structurally related epoxydictymene has been achieved: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
25. 5 The solvent-dependent stereoselectivity for the photocycloaddition of 3b has been reported: Sieburth, S. McN.; McGee Jr., K. F.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587-588.
26. 18 was followed by reduction of the nitrile to the aldehyde. Coupling 12 with the magnesium bromide acetylide derived from 2-benzyloxy-6-ethynyl pyridine and protection of the alcohol with tertbutyldimethylsilyl chloride gave 13. Hydrogenation then yields 3a. (Formula Presented)
27. 7 Sieburth, S. McN. In Advances in Cycloaddition; Harmata, M., Ed.; JAI: Greenwich, CT, 1999; Vol. 5; 85-118.
28. 8 Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
29. 9 A toluene solution of 3b (0.025M) in a pyrex test tube was strapped to the side of a water-cooled quartz immersion well surrounding a medium-pressure mercury lamp inside of a pyrex filter. The entire apparatus was placed in an ice bath during irradiation (ca. 3h). Following the irradiation, the cooled photoproduct solution was transferred to a flask and treated with an acetone solution of dimethyldioxirane (2 equivalents of a 0.07 M solution.
30. 10 Sieburth, S. McN.; Rucando, D.; Lin, C.-H. J. Org. Chem. 1999, 64, 954-959.
31. 11 Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426.
32. 12 Sera, A.; Itoh, K.; Yamaguchi, H. Tetrahedron Lett. 1990, 31, 6547-6548.
33. 13 The C12 carbinol proton in 2 is found at 4.67 ppm, presumably due to the deshielding of the adjacent carbonyl. Reduction of 8 to 9a results in a substantial upfield shift in this proton signal.
34. w) = 0.069 (0.088).
35. 15 Despite apparently ample precedent for hydride reduction of acylated ureas, we are not aware of a report concerning an effect of reducing agent concentration on product distribution. Studies in this area will be reported elsewhere.
36. 16 Fujimoto, Y.; Tatsuno, T. Tetrahedron Lett. 1976, 3325-3326.
37. Matsumoto, T.; Terao, H.; Wada, M.; Imai, S. Bull. Chem. Soc. Jpn. 1991, 64, 2762-2765.
38. 17 Paine, J. B., III J. Heterocyl. Chem. 1987, 24, 351-355.
39. 18 Hopkins, G. C.; Jonak, J. P.; Minnemeyer, H. J.; Tieckelmann, H. J. Org. Chem. 1967, 32, 4040-4044.