Concise, scalable and enantioselective total synthesis of prostaglandins View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2021-05-27

AUTHORS

Fuhao Zhang, Jingwen Zeng, Mohan Gao, Linzhou Wang, Gen-Qiang Chen, Yixin Lu, Xumu Zhang

ABSTRACT

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. More... »

PAGES

692-697

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41557-021-00706-1

DOI

http://dx.doi.org/10.1038/s41557-021-00706-1

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1138389335

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/34045714


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190 Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, China
191 rdf:type schema:Organization
192 grid-institutes:grid.4280.e schema:alternateName Department of Chemistry, National University of Singapore, Singapore, Singapore
193 schema:name Department of Chemistry, National University of Singapore, Singapore, Singapore
194 Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, China
195 rdf:type schema:Organization
 




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