Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization.
The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.
Fischer
Daniel F
DF
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Sarpong
Richmond
R
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D032502:Lycopodium / Q000378:metabolism*; D011725:Pyridines / Q000737:chemistry*
D006576:Heterocyclic Compounds, 4 or More Rings; D011725:Pyridines; C550939:complanadine A; D007495:Iridium; D002244:Carbon; D006859:Hydrogen; C023666:pyridine
J Am Chem Soc. 2009 Aug 12;131(31):11187-94
19591469
Science. 2002 Jan 11;295(5553):305-8
11719693
J Am Chem Soc. 2008 Jun 11;130(23):7222-3
18479095
Nat Prod Rep. 2004 Dec;21(6):752-72
15565253
CNS Drug Rev. 2001 Winter;7(4):353-68
11830754
J Am Chem Soc. 2002 Jan 23;124(3):390-1
11792205
Curr Med Chem. 2003 Nov;10(21):2231-52
14529340
J Org Chem. 2001 Aug 24;66(17):5901-4
11511269
Neurosci Lett. 2004 May 6;361(1-3):56-9
15135892
Zhongguo Yao Li Xue Bao. 1986 Nov;7(6):507-11
2955639
Bioorg Med Chem. 2006 Sep 1;14(17):5995-6000
16750373
J Neurosci Res. 1989 Oct;24(2):276-85
2585551
Inorg Chem. 2002 Sep 9;41(18):4798-804
12206707
Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):2089-94
11172080
Chem Commun (Camb). 2008 Jan 7;(1):91-3
18399410