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Enantioselective syntheses of heteroyohimbine natural product intermediates
US10323039B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10323039-B2 |
| Application number | US-201615145586-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 3, 2016 |
| Priority date | May 4, 2015 |
| Publication date | Jun 18, 2019 |
| Grant date | Jun 18, 2019 |
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Abstract
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Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.
First claim
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We claim: 1. A method of preparing a trans-bicyclic dihydropyran compound, said method comprising: providing a trans-piperdinyl compound of a formula wherein R 1 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 2. The method of claim 1 wherein said condensation is promoted with p-toluenesulfonic acid. 3. The method of claim 1 wherein said acylation is achieved with methyl formate and acyl chloride. 4. The method of claim 3 wherein said acid catalyst is polyphosphoric acid. 5. The method of claim 1 wherein R 1 is a tosylate (Ts) protecting group.
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to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups · CPC title
Preparation by ring-closure or hydrogenation · CPC title
- C07D491/052Primary
the oxygen-containing ring being six-membered · CPC title
by oxygen atoms · CPC title
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Frequently asked questions
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- What does patent US10323039B2 cover?
- Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.
- Who is the assignee on this patent?
- Univ Northwestern
- What technology area does this patent fall under?
- Primary CPC classification C07D491/052. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Jun 18 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).