Abstract
Amorphadiene is a natural product involved in the biosynthesis of the antimalarial drug artemisinin. A convenient four-step synthesis of amorphadiene, starting from commercially available dihydroartemisinic acid, is reported. The targeted molecule is isolated with an overall yield of 85% on a multi-gram scale in four steps with only one chromatography.
Highlights
Amorphadiene (AD) is produced in plants by cyclization of farnesyl-pyrophosphate by the enzyme amorphadiene synthase (ADS) (Scheme 1) [1]
AD is a key intermediate in the biosynthesis of the antimalarial drug artemisinin [1,2]
We report a short and high-yielding gram-scale synthesis of AD starting from the commercially available dihydroartemisinic acid, 1, which is an intermediate in the Sanofi process to prepare artemisinin [5]
Summary
Amorphadiene (AD) is produced in plants by cyclization of farnesyl-pyrophosphate by the enzyme amorphadiene synthase (ADS) (Scheme 1) [1]. AD is a key intermediate in the biosynthesis of the antimalarial drug artemisinin [1,2]. In this context, the synthesis of AD has been described using a fermentation route (Amyris process) [2e4]. We report a short and high-yielding gram-scale synthesis of AD starting from the commercially available dihydroartemisinic acid, 1, which is an intermediate in the Sanofi process to prepare artemisinin [5]. With the goal of providing a direct and scalable access to AD from the commercially available natural product dihydroartemisinic acid, 1, a three-step synthetic procedure, relying on the carboxylic acid reduction to the corresponding alcohol 2, followed by an activation/elimination sequence to produce AD, was envisioned (Scheme 2). Was reported without detailed procedures, scale, and yield for each individual step
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