Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

Daniel F. Fischer; Richmond Sarpong

doi:10.1021/ja101893b

journal article Apr 13, 2010

Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

Daniel F. Fischer Richmond Sarpong

Journal of the American Chemical Society Vol. 132 No. 17 pp. 5926-5927 · American Chemical Society (ACS)

View at Publisher Save 10.1021/ja101893b

Topics

No keywords indexed for this article. Browse by subject →

References

30

[1]

Ma X. Nat. Prod. Rep. (2004) 10.1039/b409720n

[2]

Ayer W. A. (1994)

[3]

cHudlicky, T. and Reed, J. W.InThe Way of Synthesis,1st ed.Wiley-VCH:Weinheim, Germany, 2007; pp573−602.

[4]

Tang X. C. Acta Pharmacol. Sin. (1986)

[5]

Tang X. C. J. Neurosci. Res. (1989) 10.1002/jnr.490240220

[6]

Liang Y. Q. Neurosci. Lett. (2004) 10.1016/j.neulet.2003.12.071

[7]

Jiang H. L. Curr. Med. Chem. (2003) 10.2174/0929867033456747

[8]

Woodruff-Pak D. S. Proc. Natl. Acad. Sci. U.S.A. (2001) 10.1073/pnas.98.4.2089

[9]

Shigeta M. CNS Drug Rev. (2001) 10.1111/j.1527-3458.2001.tb00204.x

[10]

Kobayashi J. J. Org. Chem. (2001) 10.1021/jo0103874

[11]

Kobayashi J. Tetrahedron Lett. (2000) 10.1016/s0040-4039(00)01630-0

[12]

Ishiuchi K. Bioorg. Med. Chem. (2006) 10.1016/j.bmc.2006.05.028

[13]

Morita H. Tetrahedron (2005) 10.1016/j.tet.2005.01.011

[14]

Bisai A. J. Am. Chem. Soc. (2008) 10.1021/ja8028069

[15]

West S. P. J. Am. Chem. Soc. (2009) 10.1021/ja903868n

[16]

The group of Prof. D. Siegel (UT Austin) has also recently completed a synthesis of4(personal communication).

[17]

Schumann D. Liebigs Ann. Chem. (1983) 10.1002/jlac.198319830206

[18]

AN IMPROVED SYNTHESIS OF 2,3,4,6,7,8-HEXAHYDROQUINOLINES

Elmar Schuster, Gerhard Jas, Dieter Schumann

Organic Preparations and Procedures International 1992 10.1080/00304949209356242

[19]

Liu K.-M. Chem. Commun. (2008) 10.1039/b714078a

[20]

Näslund G. Acta Chem. Scand. (1962) 10.3891/acta.chem.scand.16-1324

[21]

For an improved procedure, see theSupporting Information.

[22]

Kopylovich M. N. Inorg. Chem. (2002) 10.1021/ic0256720

[23]

Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate

Tatsuo Ishiyama, Jun Takagi, Kousaku Ishida et al.

Journal of the American Chemical Society 2002 10.1021/ja0173019

[24]

Remarkably Selective Iridium Catalysts for the Elaboration of Aromatic C-H Bonds

Jian-Yang Cho, Man Kin Tse, Daniel Holmes et al.

Science 2002 10.1126/science.1067074

[25]

aWe are grateful to Prof. H. Morita (Hoshi University, Japan) for1H and13C NMR spectra of4.

[26]

bComplanadine A was obtained along with small amounts ofN-Boc-lycodine (19), which presumably arises from protodeborylation.

[27]

Mori M. J. Org. Chem. (1983) 10.1021/jo00170a037

[28]

aSchneider, W. P. and McIntosh, A. V.(Upjohn). U.S. Patent 2,769,824, 1956.

[29]

VanRheenen V. Tetrahedron Lett. (1976) 10.1016/s0040-4039(00)78093-2

[30]

Ishiuchi K. Tetrahedron Lett. (2009) 10.1016/j.tetlet.2009.04.139

Cited By

231

Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

Changxia Yuan, Chih-Tsung Chang · 2013

The Journal of Organic Chemistry

Metrics

231

Citations

30

References

Details

Published: Apr 13, 2010
Vol/Issue: 132(17)
Pages: 5926-5927

Authors

D

Daniel F. Fischer

Department of Chemistry, University of California, Berkeley, California 94720

R

Richmond Sarpong

Department of Chemistry, University of California, Berkeley, California 94720

Cite This Article

Daniel F. Fischer, Richmond Sarpong (2010). Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization. Journal of the American Chemical Society, 132(17), 5926-5927. https://doi.org/10.1021/ja101893b

Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

You May Also Like