Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 39, Pages 6221-6227Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001063
Keywords
Domino reactions; One-pot reaction; Organocatalysis; Total synthesis
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Funding
- JSPS KAKENHI [JP20H04801, JP19H05630]
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Corey lactone was synthesized in a single pot within 152 minutes in a 50 % overall yield via pot and time economical manner. Latanoprost, an antiglaucoma blockbuster drug, was also synthesized via seven pot reaction with five purifications in a 25 % total yield. One of the key reactions is asymmetric domino Michael/Michael reaction, formal [3+2] cycloaddition reaction, of 3-(dimethylphenylsilyl)propenal and ethyl 4-oxo-2-pentenoate, catalyzed by diphenylprolinol silyl ether, which constructed the core substituted cyclopentanone derivative with nearly optically pure form.
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