Syntheses and X-Ray Crystal Structures of Cassiferaldehyde and Analogs

Abstract

Cassiferaldehyde, a recently discovered naturally occurring tyrosinase inhibitor, and six of its analogs, in which the aldehyde group has been replaced by various other functionalities, have been synthesized by a short and simple sequence starting from 2,3-dihydroxybenzaldehyde. Single-crystal x-ray structures of cassiferaldehyde as well as its methyl ketone, nitrile, and carboxylic acid analogs are reported.

GRAPHICAL ABSTRACT

Keywords:

• Alkylation
• bioorganic chemistry
• natural products
• phenols
• Wittig reaction

ACKNOWLEDGMENT

We thank the National Science Foundation for supporting this work through Grant No. CHE-0719335.