A concise and scalable chemoenzymatic synthesis of prostaglandins

Yunpeng Yin, Jinxin Wang and Jian Li ()
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Yunpeng Yin: Shanghai Jiao Tong University
Jinxin Wang: Second Military Medical University
Jian Li: Shanghai Jiao Tong University

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Prostaglandins have garnered significant attention from synthetic chemists due to their exceptional biological activities. In this report, we present a concise chemoenzymatic synthesis method for several representative prostaglandins, achieved in 5 to 7 steps. Notably, the common intermediate bromohydrin, a radical equivalent of Corey lactone, is chemoenzymatically synthesized in only two steps, which allows us to complete the synthesis of prostaglandin F2α in five steps on a 10-gram scale. The chiral cyclopentane core is introduced with high enantioselectivity, while the lipid chains are sequentially incorporated through a cost-effective process involving bromohydrin formation, nickel-catalyzed cross-couplings, and Wittig reactions. This cost-efficient synthesis route for prostaglandins holds the potential to make prostaglandin-related drugs more affordable and facilitate easier access to their analogues.

Date: 2024
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DOI: 10.1038/s41467-024-46960-y

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