Organic Letters
Letter
10645. (y) Ishikawa, T.; Kudo, K.; Kuroyabu, K.; Uchida, S.; Kudoh, T.;
Saito, S. J. Org. Chem. 2008, 73, 7498. (z) Suzuki, M.; Kawamoto, Y.;
Sakai, T.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2009, 11, 653.
(aa) Lajiness, J. P.; Jiang, W.; Boger, D. L. Org. Lett. 2012, 14, 2078.
(ab) Li, Z.; Zhang, S.; Wu, S.; Shen, X.; Zou, L.; Wang, F.; Li, X.; Peng,
F.; Zhang, H.; Shao, Z. Angew. Chem., Int. Ed. 2013, 52, 4117.
(ac) Nidhiry, J. E.; Prasad, K. R. Tetrahedron 2013, 69, 5525.
(ad) Mewald, M.; Medley, J. W.; Movassaghi, M. Angew. Chem., Int.
Ed. 2014, 53, 11634. (ae) Pandey, G.; Burugu, S. K.; Singh, P. Org. Lett.
2016, 18, 1558. (af) Pritchett, B. P.; Kikuchi, J.; Numajiri, Y.; Stoltz, B.
M. Angew. Chem., Int. Ed. 2016, 55, 13529. Also see ref 3h,n,o.
(5) For selected syntheses of aspidospermine in racemic form, see:
(a) Stork, G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Martin,
S. F.; Desai, S. R.; Philips, G. W.; Miller, A. C. J. Am. Chem. Soc. 1980,
102, 3294. (c) Wu, P. L.; Chu, M.; Fowler, F. W. J. Org. Chem. 1988, 53,
963. For syntheses of aspidospermine in asymmetric form, see:
(d) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673. (e) Fukuda,
Y.; Shindo, M.; Shishido, K. Org. Lett. 2003, 5, 749. (f) Shen, X.; Zhao,
R.; Mo, M.; Peng, F.; Zhang, H.; Shao, Z. J. Org. Chem. 2014, 79, 2473.
Also see ref 4j,aa.
(6) For selected syntheses of quebrachamine in racemic form, see:
(a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J.
Am. Chem. Soc. 1966, 88, 3656. (b) Ziegler, F. E.; Kloek, J. A.; Zoretic, P.
A. J. Am. Chem. Soc. 1969, 91, 2342. (c) Takano, S.; Hatakeyama, S.;
Ogasawara, K. J. Am. Chem. Soc. 1979, 101, 6414. For asymmetric
syntheses of quebrachamine in asymmetric form, see: (d) Takano, S.;
Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1981, 0, 1153.
(e) Node, M.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901.
(f) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007.
(g) Amat, M.; Lozano, O.; Escolano, C.; Molins, E.; Bosch, J. J. Org.
Chem. 2007, 72, 4431. Also see refs 3i,l, 4j,f,af, and 5a.
(7) For syntheses of cylindrocarpidine, see: (a) Saxton, J. E.; Smith, A.
J.; Lawton, G. Tetrahedron Lett. 1975, 16, 4161. (b) Lawton, G.; Saxton,
J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. Also see ref 5f.
(8) For syntheses of cimicidine, see: Satoh, H.; Ueda, H.; Tokuyama,
H. Tetrahedron 2013, 69, 89.
(9) For selected syntheses of limaspermidine, see: (a) Guerard, K. C.;
Guerinot, A.; Bouchard-Aubin, C.; Menard, M. A.; Lepage, M.; Beaulieu,
M. A.; Canesi, S. J. Org. Chem. 2012, 77, 2121. (b) Tan, S.; Banwell, M.
G.; Willis, A. C.; Reekie, T. A. Org. Lett. 2012, 14, 5621. (c) Zhang, S.;
Shen, X.; Li, Z.; Zou, L.; Wang, F.; Zhang, H.; Shao, Z. J. Org. Chem.
2013, 78, 11444. (d) Jin, J.; Qiu, F. Adv. Synth. Catal. 2014, 356, 340.
(e) Du, J.; Zeng, C.; Han, X.; Qu, H.; Zhao, X.; An, X.; Fan, C. J. Am.
Chem. Soc. 2015, 137, 4267. (f) Chen, Z.; Zhou, S.; Jia, Y. J. Org. Chem.
2015, 80, 12545.
Tung Education Foundation (141011), Program for Shanghai
Rising Star (15QA1401800), Professor of Special Appointment
(Eastern Scholar) at Shanghai Institutions of Higher Learning,
and National Program for Support of Top-notch Young
Professionals.
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■
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