Synthesis 2018; 50(09): 1901-1906
DOI: 10.1055/s-0036-1591769
paper
© Georg Thieme Verlag Stuttgart · New York

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

Vikram Gaddam
a   Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India
,
Lavanya Nadella
a   Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India
,
Genji Sukumar
a   Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India
,
Prathama S. Mainkar
b   Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India
,
a   Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India
› Author Affiliations
GV thanks DST New Delhi for INSPIRE Faculty Award (IFA14-CH-158). SC thanks Science and Engineering Research Board, Department of Science and Technology for a research grant (SB/S2/JCB-002/2015). The authors thank Council of Scientific and Industrial Research, Department of Science and Technology, Govt. of India, for research grant.
Further Information

Publication History

Received: 14 December 2017

Accepted after revision: 01 February 2018

Publication Date:
21 February 2018 (online)


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.

Supporting Information