Patent
Liphagal enantiomers and their derivatives and precursors, and enantioselective methods of making the same
| العنوان: | Liphagal enantiomers and their derivatives and precursors, and enantioselective methods of making the same |
|---|---|
| Patent Number: | 8,653,307 |
| تاريخ النشر: | February 18, 2014 |
| Appl. No: | 13/485835 |
| Application Filed: | May 31, 2012 |
| مستخلص: | Enantioenriched compositions of liphagal and its derivatives and precursors include more than 50 mol % of a first enantiomer based on the total amount of a first and a second enantiomer. A method of making an enantioenriched composition includes catalytic enantioselective alkylation, ring expansion, and intramolecular aryne cyclization. |
| Inventors: | Stoltz, Brian M (San Marino, CA, US); McFadden, Ryan (Foster City, CA, US); Virgil, Scott C. (Pasadena, CA, US); Kolding, Helene (Lyngby, DK); Alleva, Jennifer L (Princeton, NJ, US); Day, Joshua J (Fort Collins, CO, US) |
| Assignees: | California Institute of Technology (Pasadena, CA, US) |
| Claim: | 1. A method for preparing a compound of Formula 17A: [chemical expression included] comprising treating a compound of Formula 17B: [chemical expression included] under [2+2] photocycloaddition conditions with a compound represented by the Formula (I): R 29 R 30 (1) wherein: R 8 -R 16 and R 24 are independently selected from hydrogen, alkyl group and carbonyl group; R 21 and R 28 are hydrogen; and R 29 and R 30 are independently hydrogen or trialkylsilyl group. |
| Claim: | 2. A method for preparing a compound of Formula 18A: [chemical expression included] comprising treating a compound of Formula 18B: [chemical expression included] under [2+2] photocycloaddition conditions with a compound represented by the Formula (I): R 29 R 30 (1) wherein: R 8 -R 16 and R 24 are independently hydrogen or an alkyl group; R 21 and R 28 are hydrogen; and R 29 and R 30 are independently hydrogen or trialkylsilyl group. |
| Claim: | 3. The method of claim 1 or 2 , wherein R 24 is hydrogen. |
| Claim: | 4. The method of claim 1 or 2 , wherein the compound of Formula (I) is trimethylsilyl acetylene. |
| Claim: | 5. The method of claim 1 or 2 , wherein the photocycloaddition conditions comprise UV radiation. |
| Claim: | 6. The method of claim 1 or 2 , wherein the UV radiation comprises UVB radiation. |
| Claim: | 7. The method of claim 1 or 2 , wherein the photocycloaddition conditions comprise a solvent. |
| Claim: | 8. The method of claim 7 , wherein the solvent comprises acetone. |
| Claim: | 9. The method of claim 1 or 2 , wherein the method further comprises treating a compound of Formula 17A or 17B with a Lewis acid. |
| Current U.S. Class: | 568/373 |
| Patent References Cited: | WO 2006/081659 August 2006 |
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| Primary Examiner: | Chandrakumar, Nizal |
| Attorney, Agent or Firm: | Ropes & Gray LLP Halstead, David P. Pleynet, David P. |
| رقم الانضمام: | edspgr.08653307 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |