Synthesis 2016; 48(11): 1663-1683
DOI: 10.1055/s-0035-1561431
special topic
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of the C27–C35 Eribulin Fragment and Its Utilization in Building Structurally Diverse Macrocycles

Saidulu Konda
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Mahender Khatravath
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Naveen Kumar Mallurwar
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Pallavi Rao
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Shivashankar Sripelly
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Javed Iqbal*
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
,
Prabhat Arya*
Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India   Email: prabhata@drils.org   Email: prof.javediqbal@gmail.com   URL: www.prabhatarya.org
› Author Affiliations
Further Information

Publication History

Received: 10 February 2016

Accepted after revision: 17 March 2016

Publication Date:
19 April 2016 (online)

Abstract

A practical and scalable stereoselective synthesis of the western substituted tetrahydrofuran ring C27–C35 fragment of eribulin was developed by using (2S,3S)-tartaric acid as a cheap starting material that was converted into an intermediate through a stereoselective vinylation­ and cross-metathesis as the key steps. A regio- and stereo­selective intramolecular oxy-Michael cyclization or an iodocyclization reaction finally provided the required western tetrahydrofuran ring fragment and its related isomeric analogues. These key fragments were further utilized in obtaining several types of macrocyclic derivatives for exploration of their biological properties. The simplicity of our present approach has the potential to be considered for large-scale syntheses of key fragments of eribulin and related analogues.

 
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