A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine

Abstract

<p class="first" id="d23157885e65">We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet-Spengler cyclization. The present work can be considered as a formal synthesis of beta-carboline alkaloid (+/-)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids. </p>

Journal

Title: The Journal of Organic Chemistry

Abbreviated Title: J. Org. Chem.

Publisher: American Chemical Society (ACS)

ISSN (Print): 0022-3263

ISSN (Electronic): 1520-6904

Publication date Created: June 2004

Publication date (Print): June 2004

Volume: 69

Issue: 13

Pages: 4548-4550

Article

DOI: 10.1021/jo049459s

PubMed ID: 15202919

SO-VID: 6a8a1acb-cebf-40b7-8f21-988c51e91a9e

Copyright statement: © 2004

Product

Self URI (article page): https://pubs.acs.org/doi/10.1021/jo049459s