A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction

The Journal of Organic Chemistry
Rabah AzzouzFrancis Marsais

Abstract

A four-step synthesis of (-)-lentiginosine and its epimers is described starting from 2-bromopyridine. The key step consisted of a quaternarization of a fully unprotected pyridinium-polyol unit using Mitsunobu methodology. Subsequent PtO(2)-catalyzed diastereoselective hydrogenation of the pyridinium ring proceeded smoothly and led to the expected dihydroxyindolizidines with excellent yields. This stereochemically flexible strategy has been illustrated by the concise total synthesis of non-natural products derivatives such as (-)-lentiginosine and its stereoisomers in high yields.

References

Oct 16, 2001·Journal of Agricultural and Food Chemistry·D R GardnerM H Ralphs
Mar 16, 2002·The Journal of Organic Chemistry·Chuljin AhnPhilip DeShong
Aug 9, 2003·Journal of Agricultural and Food Chemistry·Mitsue HaraguchiNaoki Asano
Sep 8, 2005·Journal of the American Chemical Society·Stephan SchenkErnst Anders
Oct 29, 2005·Journal of Natural Products·John W DalyH Martin Garraffo
Jun 22, 2006·Medicinal Chemistry·F M Ruiza, J Raúl Grigera
Jul 27, 2006·Journal of the American Chemical Society·Tracy Yuen Sze But, Patrick H Toy
Dec 1, 2006·Organic Letters·Geoffrey DeguestFrancis Marsais
Jan 25, 2007·Journal of Natural Products·Tappey H JonesRoy R Snelling

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Citations

Apr 12, 2011·Journal of the American Chemical Society·Kara J StowersMelanie S Sanford
Nov 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Rajamanickam Babykala, Doraisamyraja Kalaivani
Feb 12, 2015·Beilstein Journal of Organic Chemistry·Nemai Saha, Shital K Chattopadhyay
Apr 23, 2009·Chemical Reviews·K C Kumara SwamyK V P Pavan Kumar
Oct 7, 2011·The Journal of Organic Chemistry·Donatella GiomiAlberto Brandi
Jan 25, 2018·Organic Letters·Cheng-Bo YiJin Qu

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