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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
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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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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 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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