Microwave-Assisted Claisen Rearrangement: Synthesis of Naturally Occurring TRAIL-Resistance-Overcoming Tyrosine Derivative

Abstract

Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a tumor necrosis factor (TNF) family ligand that binds on the death receptors, DR4 and DR5, activating apoptotic pathways selectively in cancer cells and thus has become a promising cancer therapeutic agent. Compound 1, isolated from Streptomyces sp. IFM 10937, has shown activity in overcoming TRAIL resistance in AGS cells. Synthesis of 1 has been accomplished from L-tyrosine in an overall high-yielding reaction sequence.

GRAPHICAL ABSTRACT

Keywords:

• Cancer
• olefin cross-metathesis reaction
• total synthesis
• TRAIL
• tyrosine derivative

ACKNOWLEDGMENT

Research facilities provided by KFUPM are gratefully acknowledged.

SUPPORTING INFORMATION

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