Download PDF
Synfacts 2014; 10(5): 0450
DOI: 10.1055/s-0033-1341100
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Mersicarpine

Contributor(s):
Erick M. Carreira
,
Hannes F. Zipfel
Lv Z, Li Z, Liang G * Nankai University, Tianjin, P. R. of China
Total Synthesis of Mersicarpine through a Cationic Cyclization Approach.

Org. Lett. 2014;
16: 1653-1655
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
17 April 2014 (online)

 
 PDF Download Permissions and Reprints

Key words

mersicarpine - indole alkaloids - Curtius rearrangement - Friedel–Crafts alkylation

Significance

Mersicarpine is an indole alkaloid isolated from plants of the genus Kopsia. Biosynthetically, Mersicarpine derives from vincadifformine and bears an unusual seven-membered cyclic imine. With their work, the authors demonstrate a short total synthesis of (±)‑mersicarpine.


#

Comment

Carboxylic acid D, obtained in five steps from A, was coupled with indole F to yield G. Exposure of carbamate G to aluminum trichloride triggered a Friedel–Crafts alkylation of the indole moiety to give H. Subsequent oxidation of H to I allowed isolation of (±)‑mersicarpine upon workup.


#
#


   Permissions and Reprints