Synlett

Process Development of Halaven®: Synthesis of the C14–C35 Fragment via Iterative Nozaki–Hiyama–Kishi Reaction–Williamson Ether Cyclization

BC Austad, F Benayoud, TL Calkins, S Campagna…

Index: Austad, Brian C.; Benayoud, Farid; Calkins, Trevor L.; Campagna, Silvio; Chase, Charles E.; Choi, Hyeong-Wook; Christ, William; Costanzo, Robert; Cutter, James; Endo, Atsushi; Fang, Francis G.; Hu, Yongbo; Lewis, Bryan M.; Lewis, Michael D.; McKenna, Shawn; Noland, Thomas A.; Orr, John D.; Pesant, Marc; Schnaderbeck, Matthew J.; Wilkie, Gordon D.; Abe, Taichi; Asai, Naoki; Asai, Yumi; Kayano, Akio; Kimoto, Yuichi; Komatsu, Yuki; Kubota, Manabu; Kuroda, Hirofumi; Mizuno, Masanori; Nakamura, Taiju; Omae, Takao; Ozeki, Naoki; Suzuki, Taeko; Takigawa, Teiji; Watanabe, Tomohiro; Yoshizawa, Kazuhiro Synlett, 2013 ,  vol. 24,  # 3  art. no. ST-2012-Y0973-C, p. 327 - 332

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Citation Number: 16

Abstract

Halaven ® (1; E7389, INN eribulin mesylate) is a fully synthetic analogue of the structurally complex marine natural product halichondrin B.[ 1 ] Eribulin has been recently approved by the FDA for the treatment of certain patients with metastatic breast cancer.[2] [3] The Halaven ® C14–C35 fragment 2 constitutes a major structural element of 1, in which 10 of the 19 stereogenic centers contained in Halaven ® are incorporated.[ 4 ] The overall approach toward 2 mirrors that ...