Concise, stereoselective route to the four diastereoisomers of 4-methylproline

Journal of Natural Products
Annabel C MurphyMurray H G Munro

Abstract

The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall yields (cumulative yields of 30-40%). Additional data on the Marfey's derivatives of the stereoisomers are also presented.

References

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Citations

Apr 21, 2010·The Journal of Organic Chemistry·Alberto PlazaCarole A Bewley
Sep 7, 2012·Journal of Natural Products·Andrea Roxanne J AnasTatsufumi Okino
May 24, 2016·Journal of Natural Products·Kazuya FukuharaShigeki Matsunaga
Feb 10, 2011·Natural Product Reports·Meng-Yuan JiangJi-Kai Liu
May 23, 2009·The Journal of Organic Chemistry·Steven G Smith, Jonathan M Goodman
Jun 10, 2010·Organic Letters·Xuguang GaoTao Ye
Aug 28, 2010·Journal of the American Chemical Society·Steven G Smith, Jonathan M Goodman
Sep 6, 2014·Organic Letters·Heather J JohnstonAlison N Hulme
Sep 25, 2018·The Journal of Organic Chemistry·Ramakotaiah MulamreddyWilliam D Lubell

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