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US 10,323,039 B2Granted
Enantioselective syntheses of heteroyohimbine natural product intermediates
AssigneeNorthwestern University
InventorsKarl A. Scheidt, Ashkaan Younai, Bi-Shun Zeng, Herbert Y. Meltzer
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Abstract
Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.
Claims5
A method of preparing a trans-bicyclic dihydropyran compound, said method comprising:
- providing a trans-piperdinyl compound of a formula
- wherein R1 is selected from H and a tosylate protecting group, wherein said trans-piperdinyl compound is provided by reacting a methyl (E)-5-(N-oxobutyl)amninopent-2-enoate with a catalytic amount of (R)-1-naphthalen-1-yl)ethanamine in the presence of an H-bond donor selected from catechol and binol;
- reduction of the ketone moiety of said piperdinyl compound to provide a hydroxy ester compound of a formula
- condensation of the hydroxy and ester moieties of said hydroxy ester compound to provide a lactone compound of a formula
- acylation of said lactone compound to provide a formyl lactone of a formula
- and
- sequential acetylation of said formyl lactone compound and acid catalyzed elimination of the carbonyl moiety of said lactone to provide a trans-bicyclic dihydropyran compound of a formula
4 more elements
Dependencies are inferred from the claim text.