Stereoselective Synthesis of Northern Fragment of Eribulin Mesylate from d-Mannose

Abstract

Stereoselective synthesis of northern fragment of eribulin mesylate is reported by coupling of the C1–C13 fragment with the C28–C35 fragment. The key steps involved in this synthesis are butyllithium-facilitated coupling between sulfone and aldehyde, then Dess–Martin periodinane oxidation followed by samarium(II) iodide mediated desulfonylation.

Key words

total synthesis - eribulin mesylate - desulfonylation - d-mannose - samarium(II) iodide

• References

• 1a Uemura D. Takahashi K. Yamamoto T. Katayama C. Tanaka J. Okumura Y. Hirata Y. J. Am. Chem. Soc. 1985; 107: 4796
• 1b Hirata Y. Uemura D. Pure Appl. Chem. 1986; 58: 701
• 2a Aicher TD. Buszek KR. Fang FG. Forsyth CJ. Jung SH. Kishi Y. Matelich MC. Scola PM. Spero DM. Yoon SK. J. Am. Chem. Soc. 1992; 114: 3162
• 2b Towle MJ. Salvato KA. Budrow J. Wels BF. Kuznetsov G. Aalfs KK. Welsh S. Zheng W. Seletsky BM. Palme MH. Habgood GJ. Singer LA. DiPietro LV. Wang Y. Chen JJ. Quincy DA. Davis A. Yoshimatsu K. Kishi Y. Yu MJ. Littlefield BA. Cancer Res. 2001; 61: 1013
• 2c Yamamoto A. Ueda A. Brémond P. Tiseni PS. Kishi Y. J. Am. Chem. Soc. 2012; 134: 893
• 2d Ueda A. Yamamoto A. Kato D. Kishi Y. J. Am. Chem. Soc. 2014; 136: 5171

For representative synthetic work
• 3a Kim S. Salomon RG. Tetrahedron Lett. 1989; 30: 6279
• 3b Burke SD. Buchanan JL. Rovin JD. Tetrahedron Lett. 1991; 32: 3961
• 3c Cooper AJ. Pan W. Salomon RG. Tetrahedron Lett. 1993; 34: 8193
• 3d Horita K. Hachiya S. Nagasawa M. Hikota M. Yonemitsu O. Synlett 1994; 38
• 3e Stamos DP. Chen SS. Kishi Y. J. Org. Chem. 1997; 62: 7552
• 3f Choi HW. Demeke D. Kang FA. Kishi Y. Nakajima K. Nowak P. Wan ZK. Xie C. Pure Appl. Chem. 2003; 75: 1
• 3g Namba K. Jun HS. Kishi Y. J. Am. Chem. Soc. 2004; 126: 7770
• 3h Zheng W. Seletsky BM. Palme MH. Lydon PJ. Singer LA. Chase CE. Lemelin CA. Shen Y. Davis H. Tremblay L. Towle MJ. Salvato KA. Wels BF. Aalfs KK. Kishi Y. Littlefield BA. Yua MJ. Bioorg. Med. Chem. Lett. 2004; 14: 5551
• 3i Namba K. Kishi Y. J. Am. Chem. Soc. 2005; 127: 15382
• 3j Lambert WT. Hanson GH. Benayoud F. Burke SD. J. Org. Chem. 2005; 70: 9382
• 3k Kaburagi Y. Kishi Y. Org. Lett. 2007; 9: 723
• 3l Henderson JA. Jackson KL. Phillips AJ. Org. Lett. 2007; 9: 5299
• 3m Zhang Z. Huang J. Ma B. Kishi Y. Org. Lett. 2008; 10: 3073
• 3n Jackson KL. Henderson JA. Motoyoshi H. Phillips AJ. Angew. Chem. Int. Ed. 2009; 48: 2346 ; and references cited therein
• 3o Chen CL. Namba K. Kishi Y. Org. Lett. 2009; 11: 409
• 3p Yu MJ. Zheng W. Seletsky BM. Nat. Prod. Rep. 2013; 30: 1158
• 4a Kishi Y. Fang FG. Forsyth CJ. Scola PM. Yoon SK. US 5436238, 1995
• 4b Stamos DP. Sean SC. Kishi Y. J. Org. Chem. 1997; 62: 7552
• 4c Seletsky BM. Wang Y. Hawkins LD. Palme MH. Habgood GJ. DiPietro LV. Towle MJ. Salvato KA. Wels BF. Aalfs KK. Kishi Y. Littlefield BA. Yu MJ. Bioorg. Med. Chem. Lett. 2004; 14: 5547
• 4d Jackson KL. Henderson JA. Phillips AJ. Chem. Rev. 2009; 109: 3044 ; and references cited therein
• 5a Stamos DP. Chen SS. Kishi Y. J. Org. Chem. 1997; 62: 7552
• 5b Chase CE. Fang FG. Lewis BM. Wilkie GD. Schnaderbeck MJ. Zhu X. Synlett 2013; 24: 323
• 5c Austad BC. Benayoud F. Calkins TL. Campagna S. Chase CE. Choi H.-W. Christ W. Costanzo R. Cutter J. Endo A. Fang FG. Hu Y. Lewis BM. Lewis MD. MeKenna S. Noland TA. Orr JD. Peasant M. Schnaderbeck MJ. Wilkie GD. Abe T. Asai N. Asai Y. Kayano A. Kimoto Y. Komastsu Y. Kubota M. Kuroda H. Mizuno M. Nakamura T. Omae T. Ozeki N. Suzuki T. Takigawa T. Watanabe T. Yoshizawa K. Synlett 2013; 24: 327
• 5d Austad BC. Calkins TL. Chase CE. Fang FG. Horstmann TE. Hu Y. Lewis BM. Niu X. Noland TA. Orr JD. Schnaderbeck MJ. Zhang H. Asakawa N. Asai N. Chiba H. Hasebe T. Hoshino Y. Ishizuka H. Kajima T. Kayano A. Komastsu Y. Kubota M. Kuroda H. Miyazawa M. Tagami K. Watanabe T. Synlett 2013; 24: 333
• 5e Lee JH. Kishi Y. J. Am. Chem. Soc. 2016; 138: 7178
• 5f Lee JH. Li Z. Osawa A. Kishi Y. J. Am. Chem. Soc. 2016; 138: 16248
• 6a Jimeno A. Clin. Cancer Res. 2009; 15: 3903
• 6b Menis J. Twelves C. Breast Cancer: Targets Ther. 2011; 3: 101 ; http://www.dovepress.com/breast-cancer---targets-and-therapy-journal
• 6c Preston JN. Trivedi MV. Ann. Pharmacother. 2012; 46: 802
• 7a Murthy AS. Mahipal B. Chandrasekhar S. Eur. J. Org. Chem. 2012; 6959
• 7b Murthy AS. Chandrasekhar S. Tetrahedron Lett. 2015; 56: 4280
• 7c Lavanya N. Kiranmai N. Mainkar PS. Chandrasekhar S. Tetrahedron Lett. 2015; 56: 4283
• 7d Chavan LN. Chegondi R. Chandrasekhar S. Tetrahedron Lett. 2015; 56: 4286
• 7e Bathula SR. Murthy AS. Mainkar PS. Chandrasekhar S. Org. Biomol. Chem. 2015; 13: 6432
• 8 Liu J. Liu Y. Zhang X. Zhang C. Gao Y. Wang L. Du Y. J. Org. Chem. 2012; 77: 9718
• 9 Ando K. J. Org. Chem. 1999; 64: 8406
• 10a Still WC. Gennari C. Tetrahedron Lett. 1983; 24: 4405
• 10b Tortosa M. Angew. Chem. Int. Ed. 2011; 50: 3950
• 11 Nicolas L. Izquierdo E. Angibaud P. Stansfield I. Meerpoel L. Reymond S. Cossy J. J. Org. Chem. 2013; 78: 11807
• 12a Rychnovsky SD. Cossrow J. Org. Lett. 2003; 5: 2367
• 12b Lambert WT. Burke SD. Org. Lett. 2003; 5: 515
• 12c Yang MT. Woerpel KA. J. Org. Chem. 2009; 74: 545
• 12d Fujioka K. Yokoe H. Yoshida M. Shishido K. Org. Lett. 2012; 14: 244
• 13 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev. 1994; 94: 2483
• 14 Horita K. Hachiya S.-I. Naitou T. Uenishi J. Yonemitsu O. Chem. Pharm. Bull. 1997; 45: 1265