Accelerating Spirocyclic Polyketide Synthesis using Flow Chemistry

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Angew. Chem. Int. Ed. 2014, volume 53, Pages 1-7

Sean Newton, Catherine F. Carter, Colin M. Pearson, Leandro de C. Alves, Heiko Lange, Praew Thansandote, and Steven V. Ley

Department of Chemistry, University of Cambridge Lensfield Road, Cambridge, CB2 1EW (UK)

Eight years after its pioneering paper on the multi-step synthesis of the oxomaritidine in flow, Steve Ley’s group publishes a new groundbreaking paper describing the total synthesis of natural products Spirodienal A and Spirangien A. The authors describe the complex synthesis of two key building blocks, where most of the 20+ steps are conducting in continuous flow, then the subsequent reactions leading to the final spirocyclic products. This synthesis was enabled by key benefits brought by Syrris Asia flow chemistry equipment such as smooth pumping of low-boiling point solvents with the Asia Pump, fast mixing in glass microreactors and continuous work-up using the Asia FLLEX. The paper illustrates how significant use of flow technology for the total synthesis of natural compounds leads to higher yields, faster processes, and improved safety.

Accelerating Spirocyclic Polyketide Synthesis using Flow Chemistry
Accelerating Spirocyclic Polyketide Synthesis using Flow Chemistry

 

Abstract: Over the past decade, the integration of synthetic chemistry with flow processing has resulted in a powerful platform for molecular assembly that is making an impact throughout the chemical community. Herein, we demonstrate the extension of these tools to encompass complex natural product synthesis. We have developed a number of novel flow-through processes for reactions commonly encountered in natural product synthesis programs to achieve the first total synthesis of spirodienal A and the preparation of spirangien A methyl ester. Highlights of the synthetic route include an iridium-catalyzed hydrogenation, iterative Roush crotylations, gold-catalyzed spiroketalization and a late-stage cis-selective reduction.

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