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Volumn 127, Issue 5, 2005, Pages 1473-1480

Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine C, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; KETONES; MARINE BIOLOGY; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 13444249603     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja040213e     Document Type: Article
Times cited : (97)

References (55)
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    • For synthesis of the putative structure 2 of lepadiformine (as a non-zwitterionic form), see: (a) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686-687. (b) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865-4873. (c) Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205-1208. (d) See also ref 6.
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    • For synthesis of the putative structure 2 of lepadiformine (as a non-zwitterionic form), see: (a) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686-687. (b) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865-4873. (c) Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205-1208. (d) See also ref 6.
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    • For synthesis of the putative structure 2 of lepadiformine (as a non-zwitterionic form), see: (a) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686-687. (b) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865-4873. (c) Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205-1208. (d) See also ref 6.
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    • See also ref 6
    • For synthesis of the putative structure 2 of lepadiformine (as a non-zwitterionic form), see: (a) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686-687. (b) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865-4873. (c) Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205-1208. (d) See also ref 6.
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    • For synthesis of the other three diastereomers of 2, see: (e) Pearson, W. H.; Barta, N. S.; Kampf, J. W. Tetrahedron Lett. 1997, 38, 3369-3372. (f) Pearson, W. H.; Ren, Y. J. Org. Chem. 1999, 64, 688-689.
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    • For synthesis of the other three diastereomers of 2, see: (e) Pearson, W. H.; Barta, N. S.; Kampf, J. W. Tetrahedron Lett. 1997, 38, 3369-3372. (f) Pearson, W. H.; Ren, Y. J. Org. Chem. 1999, 64, 688-689.
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    • For syntheses of lepadiformine (3), which appeared after establishment (ref 6) of the relative stereochemistry of lepadiformine, see: Racemic 3: (a) Sun, P.; Sun, C.; Weinreb, S. M. Org. Lett. 2001, 3, 3507-3510. (b) Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511-3514.
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    • For syntheses of lepadiformine (3), which appeared after establishment (ref 6) of the relative stereochemistry of lepadiformine, see: Racemic 3: (a) Sun, P.; Sun, C.; Weinreb, S. M. Org. Lett. 2001, 3, 3507-3510. (b) Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511-3514.
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    • For a preliminary report of a part of this work on the synthesis of lepadiformine, see ref 9
    • For a preliminary report of a part of this work on the synthesis of lepadiformine, see ref 9.
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    • When the reaction was carried out in formic acid without solvent at room temperature for 1 h, the spirocyclization was accompanied by cleavage of the N-Boc protecting group.
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    • For synthesis of (-)-cylindricine C, see: (a) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183-5187.
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    • For syntheses of (+)-cylindricine C, see: (b) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599-4602. (c) Arai, T.; Abe, H.; Aoyagi, S.: Kibayashi, C. Tetrahedron Lett. 2004, 45, 5921-5924.
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    • For syntheses of (+)-cylindricine C, see: (b) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599-4602. (c) Arai, T.; Abe, H.; Aoyagi, S.: Kibayashi, C. Tetrahedron Lett. 2004, 45, 5921-5924.
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    • For syntheses of other cylindricine alkaloids, see: (a) (±)-cyclindricine A, D, and E: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630-5633. (b) (±)-Cylindricine A and B: Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263-8266. (c) (+)-Cylidricine D and E: ref 24b.
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    • Snider, B.B.1    Liu, T.2
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    • For syntheses of other cylindricine alkaloids, see: (a) (±)-cyclindricine A, D, and E: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630-5633. (b) (±)-Cylindricine A and B: Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263-8266. (c) (+)-Cylidricine D and E: ref 24b.
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    • Liu, J.F.1    Heathcock, C.H.2
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    • note
    • For syntheses of other cylindricine alkaloids, see: (a) (±)-cyclindricine A, D, and E: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630-5633. (b) (±)-Cylindricine A and B: Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263-8266. (c) (+)-Cylidricine D and E: ref 24b.
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    • Personal communication
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.