Synthesis, Table of Contents Synthesis 2021; 53(22): 4178-4186DOI: 10.1055/a-1403-4312 special topic Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award Total Synthesis of Mycocyclosin and the Herqulines Authors Jonathon S. Ryan Corinna S. Schindler∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract Since the first reports of their isolation, mycocyclosin and the herquline family of natural products have attracted interest from the synthetic community for their uniquely strained macrocyclic architectures. This review describes the attempted and successful total syntheses of these natural products and provides a summary of the strategies developed in the years since their isolation. 1 Introduction 2 Biosynthesis 3 Early Studies 4 Total Synthesis of Mycocyclosin 5 Overview 6 Wood’s Total Syntheses of Herqulines B and C 7 Baran’s Total Syntheses of Herqulines B and C 8 Schindler’s Total Syntheses of Herqulines B and C 9 Conclusions Key words Key wordstotal synthesis - herqulines - macrocycles - strain - Birch reduction Full Text References References 1 Ōmura S, Hirano A, Iwai Y, Masuma R. J. Antibiot. 1979; 32: 786 2 Furusaki A, Matsumoto T, Ogura H, Takayanagi H, Hirano A, Ōmura S. J. Chem. Soc., Chem. Commun. 1980; 698 3 Enomoto Y, Shiomi K, Hayashi M, Masuma R, Kawakubo T, Tomosawa K, Iwai Y, Ōmura S. J. Antibiot. 1996; 49: 50 4 Cox JB, Kimishima A, Wood JL. J. Am. Chem. Soc. 2019; 141: 25 5 Yu X, Liu F, Zou Y, Tang MC, Hang L, Houk KN, Tang Y. J. Am. Chem. Soc. 2016; 138: 13529 6 Belin P, Le Du MH, Fielding A, Lequin O, Jacquet M, Charbonnier J.-B, Lecoq A, Thai R, Courçon M, Masson C, Dugave C, Genet R, Pernodet J.-L, Gondry M. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 7426 7 Cochrane JR, White JM, Wille U, Hutton CA. Org. Lett. 2012; 14: 2402 8 Yang H. PhD Thesis . University of Birmingham; UK: 2015 9 Zhu X, McAtee CC, Schindler CS. Org. Lett. 2018; 20: 2862 10 Kim GT. PhD Thesis . Korea Advanced Institute of Science and Technology; Republic of Korea: 1997 11 Kawai N, Atsumi T, Arai N, Kuwajima I. Nippon Kagakkai Koen Yokoshu 2003; 777 12 Hart JM. PhD Thesis . University of Leeds; UK: 2004 13 Stawski PS. PhD Thesis . Ludwigs-Maximilians-Universitat Munchen; Germany: 2012 14 Volpin G. PhD Thesis . Ludwigs-Maximilians-Universitat Munchen; Germany: 2017 15 Carbonnelle AC, Zhu J. Org. Lett. 2000; 2: 3477 16 Hutton CA, Skaff O. Tetrahedron Lett. 2003; 44: 4895 17 Skaff O, Jolliffe KA, Hutton CA. J. Org. Chem. 2005; 70: 7353 18 Carreira EM, Imhof MA. Synfacts 2019; 15: 0224 19 He C, Stratton TP, Baran PS. J. Am. Chem. Soc. 2019; 141: 29 20 Cheng C, Brookhart M. J. Am. Chem. Soc. 2012; 134: 11304 21 Zhu X, McAtee CC, Schindler CS. J. Am. Chem. Soc. 2019; 141: 3409 22 Zanda M. Synform 2019; 7: A102 23 Goldstein DM, Wipf P. Tetrahedron Lett. 1996; 37: 739 24 Rama Rao AV, Gurjar MK, Sharma PA. Tetrahedron Lett. 1991; 32: 6613 25 Hara H, Inoue T, Nakamura H, Endoh M, Hoshino O. Tetrahedron Lett. 1992; 33: 6491 26 Quideau S, Pouységu L, Avellan AV, Whelligan DK, Looney MA. Tetrahedron Lett. 2001; 42: 7393 27 Mikami K, Yamaoka M, Yoshida A, Nakamura Y, Takeuchi S, Ohgo Y. Synlett 1998; 607 28 Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem. Int. Ed. 2009; 48: 9507 29 Cotsaris E, Paddon-Row MN. J. Chem. Soc., Chem. Commun. 1982; 1206
