Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones

Chemical Science - Tập 8 Số 9 - Trang 6202-6206
Xiao‐Dong Zuo1,2,3,4,5, Shu‐Min Guo1,2,3,4,5, Rui Yang1,2,3,4,5, Jian‐Hua Xie1,2,3,4,5, Qi‐Lin Zhou1,6,2,4,5
1China
2College of Chemistry
3Nankai University;
4State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China
5Tianjin 300071
6Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China

Tóm tắt

A bioinspired enantioselective synthesis of crinine-type alkaloids was developed by iridium-catalyzed asymmetric hydrogenation of enones, providing 24 crinine-type alkaloids and 8 analogues with high yield and high enantioselectivity.

Từ khóa


Tài liệu tham khảo

Nair, 2013, Nat. Prod. Commun., 8, 1335

Z. Jin and X.-H.Xu, in Natural Products: Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes, ed. K. G. Ramawat and J. M. Mérillon, Springer-Verlag, Berlin Heidelberg, 2013, p. 479

Ding, 2016, J. Asian Nat. Prod. Res., 12, 1

Williams, 2011, Nat. Prod. Rep., 28, 48, 10.1039/C0NP00027B

Masone, 1955, J. Am. Chem. Soc., 77, 1253, 10.1021/ja01610a046

Boit, 1956, Chem. Ber., 89, 1129, 10.1002/cber.19560890509

Feistein, 1976, J. Org. Chem., 41, 2447, 10.1021/jo00876a020

Kilgore, 2016, Phytochem. Rev., 15, 317, 10.1007/s11101-015-9451-z

Muxfeldt, 1966, J. Am. Chem. Soc., 88, 3670, 10.1021/ja00967a052

Whitlock, 1967, J. Am. Chem. Soc., 89, 3600, 10.1021/ja00990a045

Stevens, 1972, J. Org. Chem., 37, 977, 10.1021/jo00972a012

Keck, 1981, J. Am. Chem. Soc., 103, 3173, 10.1021/ja00401a039

Sánchez, 1983, J. Am. Chem. Soc., 105, 7640, 10.1021/ja00364a029

Martin, 1987, Tetrahedron Lett., 28, 503, 10.1016/S0040-4039(00)95766-6

Pearson, 1994, Tetrahedron Lett., 35, 9173, 10.1016/0040-4039(94)88457-9

Bru, 2003, Org. Lett., 5, 1845, 10.1021/ol0343358

Kodama, 2004, Tetrahedron, 60, 4901, 10.1016/j.tet.2004.03.087

Bru, 2006, Tetrahedron, 62, 9043, 10.1016/j.tet.2006.07.005

Anwar, 2008, Synlett, 2681

Tam, 2008, Org. Lett., 10, 601, 10.1021/ol702907u

Bogle, 2010, Org. Lett., 12, 1252, 10.1021/ol1000654

Boglea, 2010, Tetrahedron, 66, 6399, 10.1016/j.tet.2010.04.132

Yamada, 1976, Tetrahedron Lett., 17, 57, 10.1016/S0040-4039(00)71322-0

Tomioka, 1977, Chem. Pharm. Bull., 25, 2681, 10.1248/cpb.25.2681

Overman, 1985, Helv. Chim. Acta, 68, 745, 10.1002/hlca.19850680324

Kita, 1996, J. Org. Chem., 61, 5857, 10.1021/jo9606766

Bohno, 2004, Chem. Commun., 1086, 10.1039/b402762k

Bohno, 2007, Tetrahedron, 63, 6977, 10.1016/j.tet.2007.05.041

Rousseau, 2014, Chem.–Eur. J., 20, 14771, 10.1002/chem.201403662

Wei, 2013, Chem.–Asian J., 8, 1966, 10.1002/asia.201300595

Lyle, 1960, J. Am. Chem. Soc., 82, 2625, 10.1021/ja01495a057

Viladomat, 1995, Phytochemistry, 40, 307, 10.1016/0031-9422(95)00191-9

Kagan, 2001, Tetrahedron, 57, 2449, 10.1016/S0040-4020(01)00065-5

Vedejs, 2005, Angew. Chem., Int. Ed., 44, 3974, 10.1002/anie.200460842

Miller, 2011, Chem. Soc. Rev., 40, 4550, 10.1039/c1cs15069c

Reynolds, 2005, Tetrahedron, 61, 6368, 10.1016/j.tet.2005.03.121

Jana, 2007, Angew. Chem., Int. Ed., 46, 6542, 10.1002/anie.200701631

Miller, 2009, Angew. Chem., Int. Ed., 48, 2398, 10.1002/anie.200806154

Lian, 2010, J. Am. Chem. Soc., 132, 12422, 10.1021/ja103916t

Samanta, 2010, J. Org. Chem., 75, 1101, 10.1021/jo9022099

Noyori, 2001, Angew. Chem., Int. Ed., 40, 40, 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5

Arai, 2008, Angew. Chem., Int. Ed., 47, 7457, 10.1002/anie.200802533

Shimizu, 2009, Synlett, 3143, 10.1055/s-0029-1218347

Xie, 2010, J. Am. Chem. Soc., 132, 4538, 10.1021/ja100652f

Zhang, 2012, Org. Lett., 14, 6158, 10.1021/ol302842h

Chen, 2014, Org. Lett., 16, 3912, 10.1021/ol501648a

Ohkuma, 1995, J. Am. Chem. Soc., 117, 10417, 10.1021/ja00146a041

Ohkuma, 1997, Synlett, 467, 10.1055/s-1997-6141

Ohkuma, 2004, Org. Lett., 6, 2681, 10.1021/ol049157c

Xie, 2011, Angew. Chem., Int. Ed., 50, 7329, 10.1002/anie.201102710

Xie, 2012, Angew. Chem., Int. Ed., 51, 201, 10.1002/anie.201105780

Wildman, 1958, J. Am. Chem. Soc., 80, 2567, 10.1021/ja01543a053

Chen, 2011, J. Nat. Prod., 74, 411, 10.1021/np100819n

Irie, 1968, J. Chem. Soc. C, 1802, 10.1039/j39680001802

Kihara, 1987, Chem. Pharm. Bull., 35, 1070, 10.1248/cpb.35.1070

Abou-Donia, 2002, Planta Med., 68, 379, 10.1055/s-2002-26754

Pabuççuoğlu, 1989, J. Nat. Prod., 52, 785, 10.1021/np50064a020

Machocho, 1999, Phytochemistry, 51, 1185, 10.1016/S0031-9422(99)00118-1

Likhitwitayawuid, 1991, J. Nat. Prod., 56, 1331, 10.1021/np50098a017

Pham, 1998, Phytochemistry, 48, 371, 10.1016/S0031-9422(97)01081-9

Ali, 1986, Phytochemistry, 25, 2399, 10.1016/S0031-9422(00)81704-5

Machocho, 2004, Phytochemistry, 65, 3143, 10.1016/j.phytochem.2004.10.004