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

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

Research output: Contribution to journalArticle

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

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Bioactivity
Biological Products
Bearings (structural)
Anthozoa
Structure-Activity Relationship
synthesis
Cytotoxicity
products
musculoskeletal system
Skeleton
routes
expansion
rings
rameswaralide

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide : Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores. / Truax, Nathanyal J.; Ayinde, Safiat; Van, Khoi; Liu, Jun; Romo, Daniel.

In: Organic Letters, Vol. 21, No. 18, 20.09.2019, p. 7394-7399.

Research output: Contribution to journalArticle

Truax, Nathanyal J. ; Ayinde, Safiat ; Van, Khoi ; Liu, Jun ; Romo, Daniel. / Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide : Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores. In: Organic Letters. 2019 ; Vol. 21, No. 18. pp. 7394-7399.
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