Short and flexible route to 3,4-diarylpyrrole marine alkaloids: Syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4443-4446

  Iwao, Masatomo ^a   Takeuchi, Toshiro ^a   Fujikawa, Naotaka ^a   Fukuda, Tsutomu ^a   Ishibashi, Fumito ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; LAMELLARIN G TRIMETHYL ETHER; NINGALIN B; PALLADIUM; PERMETHYLSTORNIAMIDE A; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DECARBOXYLATION; DEMETHYLATION; DRUG SYNTHESIS; POLYMERIZATION; RING CLOSING METATHESIS; STOICHIOMETRY;

LATEOLABRAX JAPONICUS;

EID: 0038066152     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01031-1     Document Type: Article

References (49)

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19. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
20. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
21. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
22. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
23. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
24. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
25. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
26. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
27. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
28. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
29. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
30. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
31. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
32. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
33. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
34. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
35. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
36. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
37. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
38. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
39. Pentacyclic lamellarins: (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155; (b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951; (c) Banwell, M.; Flynn, B.; Hockless, D. J. Chem. Soc., Chem. Commun. 1997, 2259; (d) Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755; (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147; (f) Ruchirawat, S.; Mutarapat, T. Tetrahedron Lett. 2001, 42, 1205; (g) Diaz, M.; Guitian, E.; Castedo, L. Synlett 2001, 1164; (h) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500; (i) Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285; (j) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363. Simple 3,4-diarylpyrrole alkaloids: (k) Fürstner, A.; Weintritt, H.; Huppers, A. J. Org. Chem. 1995, 60, 6637; (l) Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941; (m) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. J. Chem. Soc., Chem. Commun. 1997, 207; (n) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165; (o) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515; (p) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587; (q) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477; (r) Kim, S.; Son, S.; Kang, H. Bull. Korean Chem. Soc. 2001, 22, 1403; (s) Namsa-aid, A.; Ruchirawat, S. Org. Lett. 2002, 4, 2633; (t) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287; (u) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373; (v) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
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