Total synthesis of cis-solamin

Organic Letters
Hidefumi MakabeTakayuki Oritani

Abstract

[structure: see text] A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)2-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.

References

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Citations

Jan 27, 2004·Bioorganic & Medicinal Chemistry Letters·Hiroyuki KonnoHideto Miyoshi
Apr 5, 2005·Natural Product Reports·Almudena BermejoDiego Cortes
Nov 18, 2005·Chemical Communications : Chem Comm·Yulai Hu, Richard C D Brown
Oct 12, 2007·Bioscience, Biotechnology, and Biochemistry·Hidefumi Makabe
Feb 5, 2009·Beilstein Journal of Organic Chemistry·Nianguang LiXiang Li
Aug 27, 2016·The Journal of Organic Chemistry·Juliane Adrian, Christian B W Stark
Dec 15, 2004·Angewandte Chemie·Gillian L NattrassSteven V Ley
Jul 28, 2006·Organic Letters·Hülya Göksel, Christian B W Stark
Apr 11, 2018·Organic & Biomolecular Chemistry·Koichiro OtaHiroaki Miyaoka
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Juliane AdrianChristian B W Stark
Sep 26, 2020·Chemistry, an Asian Journal·Rodney A FernandesPriyanka Choudhary
Nov 8, 2014·Organic Letters·Juliane Adrian, Christian B W Stark

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