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

Vikram Gaddam; Lavanya Nadella; Genji Sukumar; Prathama S. Mainkar; Srivari Chandrasekhar

doi:10.1055/s-0036-1591769

Synthesis, Table of Contents

Synthesis 2018; 50(09): 1901-1906
DOI: 10.1055/s-0036-1591769

paper

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

Vikram Gaddam

^aNatural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India

,

Lavanya Nadella

^aNatural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India

^cAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India

,

Genji Sukumar

^aNatural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India

,

Prathama S. Mainkar

^bMedicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India

^cAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India

,

Srivari Chandrasekhar *

^aNatural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India

^cAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110 020, India

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Abstract

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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

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References

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