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Enantioselective syntheses of heteroyohimbine natural product intermediates
US10654865B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10654865-B2 |
| Application number | US-201916439638-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 12, 2019 |
| Priority date | May 4, 2015 |
| Publication date | May 19, 2020 |
| Grant date | May 19, 2020 |
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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 cis-bicyclic dihydropyran compound, said method comprising: providing a hydroxy ester compound of a formula dehydration and reprotection of said hydroxy ester compound to provide an alkene compound of a formula and hydroboration of said alkene compound to promote formation of a lactone compound of a formula and acylation of said lactone compound and subsequent treatment with an acid catalyst to provide a cis-bicyclic dihydropyran compound of a formula 2. The method of claim 1 wherein said dehydration is achieved with sodium iodide. 3. The method of claim 1 wherein said reprotection is achieved with magnesium metal and benzyl carbamate. 4. The method of claim 1 wherein said hydroboration is achieved with 9-borabicyclo[3.3.1]nonane (9-BBN). 5. The method of claim 1 wherein said acylation is achieved with sodium hydride and acyl chloride. 6. The method of claim 5 wherein said acid catalyst is p-toluenesulfonic acid. 7. The method of claim 1 further comprising removing said benzyl carbamate protecting group by hydrogenating said cis-bicyclic dihydropyran compound over palladium-carbon.
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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 US10654865B2 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 May 19 2020 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).