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

Srinath Pashikanti, Rehnman Ukani, Sunil A. David, Apurba Datta

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.

Original languageEnglish (US)
Article numberss-2016-m0623-op
Pages (from-to)2088-2100
Number of pages13
JournalSynthesis (Germany)
Volume49
Issue number9
DOIs
StatePublished - May 3 2017

Bibliographical note

Publisher Copyright:
© Georg Thieme Verlag Stuttgart · New York-Synthesis 2017.

Keywords

  • cytotoxic
  • drug development
  • jaspine B
  • stereochemistry
  • structure-activity relationships

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