A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

Shen H Tan; Martin G Banwell; Anthony C Willis

doi:10.1021/acs.joc.6b01400

A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

J Org Chem. 2016 Sep 2;81(17):8022-8. doi: 10.1021/acs.joc.6b01400. Epub 2016 Jul 27.

Authors

Shen H Tan¹, Martin G Banwell¹, Anthony C Willis¹

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.

PMID: 27419257
DOI: 10.1021/acs.joc.6b01400

Abstract

Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cobalt / chemistry*
Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Magnetic Resonance Spectroscopy / methods
Oxidation-Reduction
Quinolones / chemistry*
Spectrometry, Mass, Electrospray Ionization

Substances

Heterocyclic Compounds, 4 or More Rings
Quinolones
kopsihainanine A
Cobalt