We have developed an innovative strategy for the formation of angular carbocycles via a gold(I)-catalyzed dehydro Diels-Alder reaction. This transformation provides rapid access to a variety of complex angular cores in excellent diastereoselectivities and high yields. The usefulness of this Au -catalyzed cycloaddition was further demonstrated by accomplishing a 11-steps total synthesis of (±)-magellanine.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201611606 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses of Scabrolide B, Ineleganolide, and Related Norcembranoids.
J Am Chem Soc
December 2024
Department of Chemistry, Rice University, Houston, Texas 77005, United States.
Concise total syntheses of several 5/7/6 norcembranoids, including ineleganolide, scabrolide B, sinuscalide C, and fragilolide A have been achieved through a fragment coupling/ring closure approach. The central seven-membered ring was forged through sequential Mukaiyama-Michael/aldol reactions using norcarvone and a decorated bicyclic lactone incorporating a latent electrophile. Subsequent manipulations installed the reactive enedione motif and delivered scabrolide B in 11 steps from a chiral pool-derived enone.
View Article and Find Full Text PDFConcise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.
Synthesis (Stuttg)
January 2024
Department of Chemistry, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, USA.
alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management.
View Article and Find Full Text PDFThe Asymmetric Total Synthesis of the Female-Produced Sex Pheromone of the Tea Tussock Moth.
Molecules
August 2024
Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China.
The tea tussock moth is a pest that damages tea leaves, affecting the quality and yield of tea and causing huge economic losses. The efficient asymmetric total synthesis of the sex pheromone of the tea tussock moth was achieved using commercially available starting materials with a 25% overall yield in 11 steps. Moreover, the chiral moiety was introduced by Evans' template and the key C-C bond construction was accomplished through Julia-Kocienski olefination coupling.
View Article and Find Full Text PDFStereodivergent Total Synthesis of Ethyl Plakortide Z.
Org Lett
July 2024
BioCIS, Faculté de Pharmacie, Université Paris-Saclay, CNRS, 91400 Orsay France.
Plakortides make up a subclass of marine endoperoxides with diverse biological activities. Their structural particularity is derived from the C and C positions of the endoperoxide, which are substituted by ethyl groups. The ethyl plakortide Z has the simplest side chain among its congeners and is an excellent target for testing a universal strategy for the synthesis of this subfamily.
View Article and Find Full Text PDFTotal Synthesis of (15R)- and (15S)-Prostaglandin A.
Chemistry
September 2024
Department of Pharmaceutical Sciences, University of Vienna, Josef-Holaubek-Platz 2, 1090, Vienna, Austria.
From both pharmaceutical and structural perspectives, the large family of prostaglandins represent a truly remarkable class of natural products. Prostaglandin A is a tissue hormone naturally found in human seminal plasma and in the sea whip Plexaura homomalla with yet poorly understood biological or therapeutic effects. Herein, a novel strategy for the stereoselective construction of both naturally occurring prostaglandin A epimers and first insights into their functional effects on the major inhibitory neurotransmitter γ-aminobutyric acid (GABA) type A receptors (GABAR) are provided.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!