Synthesis of (+)-Didemniserinolipid B: Application of a 2-Allyl-4-fluorophenyl Auxiliary for Relay Ring-Closing Metathesis
| Autor: | Eric A. Voight, Steven D. Burke, Christopher L. Paradise, Judy M. Suh, Christopher C. Marvin |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule Alkene Organic Chemistry Total synthesis Alkenes Octanes Metathesis Combinatorial chemistry Chemical synthesis Article Bridged Bicyclo Compounds chemistry.chemical_compound Ring-closing metathesis chemistry Cyclization Propylene Glycols Dihydroxylation Octene |
| Zdroj: | The Journal of Organic Chemistry. 73:8452-8457 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The synthesis of didemniserinolipid B utilizing a ketalization/ring-closing metathesis (K/RCM) strategy is described. In the course of this work, a novel 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis (RRCM) was developed, which increased the yield of the RCM. The resulting 6,8-dioxabicyclo[3.2.1]octene core was selectively functionalized by complimentary dihydroxylation and epoxidation routes to install the C10 axial alcohol. This bicyclic ketal core was further functionalized by etherification and an alkene cross metathesis with an unsaturated alpha-phenylselenyl ester en route to completing the total synthesis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|