Synthesis 2017; 49(09): 2088-2100
DOI: 10.1055/s-0036-1588118
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis and Structure–Activity Relationship Studies of the Cytotoxic Anhydrophytosphingosine Jaspine B (Pachastrissamine)

Srinath Pashikanti, Rehnman Ukani, Sunil A. David, Apurba Datta*
  • Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA   Email: adutta@ku.edu
Further Information

Publication History

Received: 09.09.216Received: 09.09.216

Accepted after revision: 16 November 2016

Publication Date:
19 December 2016 (eFirst)

Dedicated to Professor Hiriyakkanavar Junjappa on the occasion of his 80th birthday

Abstract

By utilizing an l-serine-derived bicyclic lactone as an advanced chiral building block, a short synthetic route to the cytotoxic marine natural product jaspine B has been developed. Targeting structure–activity relationship investigations, the synthetic route has also been utilized for the synthesis and cytotoxicity evaluation of strategically modified jaspine B analogues. In addition, a previously reported synthesis of the title natural product from our research has been reinvestigated to clarify the sterochemical assignment.

Supporting Information