Methyl‐jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatürlichen Enantiomer via Palladium(0)‐induzierte, enantiodivergente Alkylierung von Cyclopent‐2‐en‐1,3‐diol‐Derivaten
- 13 December 1989
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 72 (8) , 1852-1859
- https://doi.org/10.1002/hlca.19890720822
Abstract
Methyl Jasmonate: A Short Synthesis of Naturally Occurring Methyl Jasmonate and its Unnatural Enantiomer via Enantiodivergent Alkylation of Cyclopent‐2‐ene‐1,3‐diol Derivatives by Palladium(0)‐Induced ReactionsPalladium‐catalyzed alkylation of cyclopent‐2‐ene‐1,2‐diol derivatives like 2 is a useful method for enantiodivergent functionalization, resulting in both enantiomeric series of chiral building blocks. The chiral building blocks 3 and 13 can be transformed to methyl jasmonate (1)and its unnatural enantiomer ent‐1, recent statement [1b] that 1 has no odour at all and that ‘methyl jasmonate's’ fragrance is actually due to its cis‐isomer ent‐11 has been confirmed also for the enantiomeric series.This publication has 39 references indexed in Scilit:
- Synthesis of (1S,4R)-(-)-4-Hydroxy-2-cyclopentenyl Acetate by a Highly Enantioselective Enzyme-Catalyzed Transesterification in Organic SolventsSynthesis, 1988
- Chemie und Stereochemie der Iridoide, IX. EPC‐Synthese von (1R,2R,2″Z)‐(−)‐Methyl‐jasmonat aus Catalpol – Kristall‐ und Molekularstruktur von Methyl‐dehydrojasmonat‐semicarbazonEuropean Journal of Organic Chemistry, 1987
- Mit (+)-8-Phenylneomenthol zum enantiomerenreinen (−)-MethyljasmonatAngewandte Chemie, 1986
- Prostaglandin‐Synthesen durch Dreikomponenten‐KupplungAngewandte Chemie, 1984
- Organopalladium Compounds in Organic Synthesis and in CatalysisPublished by Elsevier ,1982
- Asymmetric synthesis of a prostaglandin intermediate using micro-organismsJournal of the Chemical Society, Chemical Communications, 1976
- New synthetic reactions. Catalytic vs. stoichiometric allylic alkylation. Stereocontrolled approach to steroid side chainJournal of the American Chemical Society, 1976
- Applications of Diisobutylaluminium Hydride (DIBAH) and Triisobutylaluminium (TIBA) as Reducing Agents in Organic SynthesisSynthesis, 1975
- Applications of Diisobutylaluminium Hydride (DIBAH) and Triisobutylaluminium (TIBA) as Reducing Agents in Organic SynthesisSynthesis, 1975
- Über Säureamidacetale, Harnstoffacetale und LactamacetaleEuropean Journal of Organic Chemistry, 1961