Asymmetric total synthesis of prostaglandin C<sub>2</sub> TBS ether

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.

show abstract

Organocatalyst-mediated, pot-economical total synthesis of latanoprost

Kawauchi¹,

Suga²,

Toda³

et al. 2023

Chem. Sci.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Asymmetric total synthesis of prostaglandin C₂ TBS ether

Abstract: We disclose an asymmetric total synthesis of prostaglandin C2 TBS ether, a derivative of an extremely sensitive natural prostaglandin C2. The key to the synthesis is a SmI2-mediated ketyl−enoate reaction...

Cited by 4 publications

References 57 publications

Grignard Reaction: An ‘Old-Yet-Gold’ synthetic gadget toward the synthesis of natural Products: A review

Grignard Reaction: An ‘Old-Yet-Gold’ synthetic gadget toward the synthesis of natural Products: A review

A concise and scalable chemoenzymatic synthesis of prostaglandins

Organocatalyst-mediated, pot-economical total synthesis of latanoprost

Contact Info

Product

Resources

About

Asymmetric total synthesis of prostaglandin C2 TBS ether

Abstract: We disclose an asymmetric total synthesis of prostaglandin C2 TBS ether, a derivative of an extremely sensitive natural prostaglandin C2. The key to the synthesis is a SmI2-mediated ketyl−enoate reaction...

Cited by 4 publications

References 57 publications

Grignard Reaction: An ‘Old-Yet-Gold’ synthetic gadget toward the synthesis of natural Products: A review

Grignard Reaction: An ‘Old-Yet-Gold’ synthetic gadget toward the synthesis of natural Products: A review

A concise and scalable chemoenzymatic synthesis of prostaglandins

Organocatalyst-mediated, pot-economical total synthesis of latanoprost

Contact Info

Product

Resources

About

Asymmetric total synthesis of prostaglandin C₂ TBS ether