Synthesis 2024; 56(03): 462-468
DOI: 10.1055/a-2202-5597
paper

A Convergent Approach for the Synthesis of C14–C26 Fragment of Anticancer Drug Eribulin Mesylate

Authors

  • Rajesh Nasam

    a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Uppal Road, Hyderabad-500007, Telangana, India
    b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
  • Srihari Pabbaraja

    a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Uppal Road, Hyderabad-500007, Telangana, India
    b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

The authors thanks CSIR, New Delhi for funding this project under mission INPROTICS.


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Abstract

The stereoselective synthesis of C14–C26 fragment of eribulin is reported in a convergent way by coupling of fragment C14–C19 with fragment C20–C26 that are accessible from commercially available raw materials crotonic acid and 1,4-butanediol. The key steps involved in this practical approach are Hosomi–Sakurai asymmetric alkylation, Maruoka allylation, Noyori reduction, silver-catalyzed one-pot rearrangement, and intramolecular cyclization.

Supporting Information



Publication History

Received: 01 August 2023

Accepted after revision: 02 November 2023

Accepted Manuscript online:
02 November 2023

Article published online:
29 November 2023

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