Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores

Nathanyal J. Truax, Safiat Ayinde, Khoi Van, Jun O. Liu, Daniel Romo

Research output: Contribution to journalArticlepeer-review

Abstract

A pharmacophore-directed retrosynthesis strategy applied to rameswaralide provided simplified precursors bearing the common 5,5,6 (red) and 5,5,7 (blue) skeleton present in several cembranoid and norcembranoids from Sinularia soft corals. Key steps include a Diels-Alder lactonization organocascade delivering the common 5,5,6 core and a subsequent ring expansion affording a 5,5,7 core serviceable for the synthesis of rameswaralide. Initial structure-activity relationships of intermediates en route to the natural product have revealed interesting differential and selective cytotoxicity.

Original languageEnglish (US)
Pages (from-to)7394-7399
Number of pages6
JournalOrganic Letters
Volume21
Issue number18
DOIs
StatePublished - Sep 20 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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