Synlett 2013; 24(3): 327-332
DOI: 10.1055/s-0032-1317920
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© Georg Thieme Verlag Stuttgart · New York

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

Brian C. Austada, Farid Benayouda, Trevor L. Calkinsa, Silvio Campagnaa, Charles E. Chase*a, Hyeong-wook Choia, William Christa, Robert Costanzoa, James Cuttera, Atsushi Endoa, Francis G. Fanga, Yongbo Hua, Bryan M. Lewisa, Michael D. Lewisa, Shawn McKennaa, Thomas A. Nolanda, John D. Orra, Marc Pesanta, Matthew J. Schnaderbecka, Gordon D. Wilkiea, Taichi Abeb, Naoki Asaib, Yumi Asaib, Akio Kayanob, Yuichi Kimotob, Yuki Komatsub, Manabu Kubotab, Hirofumi Kurodab, Masanori Mizunob, Taiju Nakamurab, Takao Omaeb, Naoki Ozekib, Taeko Suzukib, Teiji Takigawab, Tomohiro Watanabeb, Kazuhiro Yoshizawab
  • aPharmaceutical Science & Technology, Eisai Product Creation Systems, Eisai Inc., 4 Corporate Drive, Andover, MA 01810-2441, USA   Fax: +1(978)7944910   Email: Charles_Chase@eri.eisai.com
  • bPharmaceutical Science & Technology, Eisai Product Creation Systems, Eisai Co., Ltd., 22 Sunayama, Kamisu-Shi, Ibaraki 314-0255, Japan
Further Information

Publication History

Received: 13 November 2012

Accepted: 22 November 2012

Publication Date:
10 January 2013 (eFirst)

Abstract

Multikilogram manufacturing process of the Halaven® C14–C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment.

Primary Data