A versatile approach to 6-substituted-5-methoxy-δ-lactam framework and application to the formal synthesis of (±)-homopumiliotoxin 223G

Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

“…Compound 11g was protected with TBSCl (imid., DMAP, CH 2 Cl 2 ) to produce TBS ether 12 , whose spectral data were identical with those reported. , The synthesis of 12 constitutes a formal synthesis of (−)-deoxoprosophylline ( 13 ) . In addition, Rapoport and co-workers have converted ent - 11g into 14 ; moreover, 14 is a versatile intermediate that can be elaborated to 15 , 16 , and 17 (Scheme ) …”

Direct Stereoselective β‐Arylation of Enol Ethers by a Decarboxylative Heck‐Type Reaction

“…Our investigation about the β‐arylation of ethyl 2‐methoxyacrylate 1A by Pd‐catalyzed decarboxylative Heck‐type coupling was initiated with 2‐methoxybenzoic acid 2a . Choice of the coupling partner 2a was driven by the steric hindrance and the electronic nature of the ortho ‐methoxy substituent, two factors which are known to facilitate the decarboxylative step .…”

“…Mass analysis (ESI) were performed on a LCQ Advantage. Ethyl 2‐methoxyacrylate 1A , 2‐(1,1‐dimethylethyl)‐5‐methylene‐1,3‐dioxolan‐4‐one 1B are synthetized according to the literature.…”

Asymmetric Synthesis of (−)-1-Hydroxyquinolizidinone, a Common Intermediate for the Syntheses of (−)-Homopumiliotoxin 223G and (−)-Epiquinamide

“…On the other hand, very few syntheses of homopumiliotoxins and more particularly of (+)- or (−)-homopumiliotoxin 223G (2a) are reported. Indeed, to the best of our knowledge, only two total asymmetric syntheses of (+)-homopumiliotoxin 223G (2a) have been disclosed. , Its antipode ent- 2a has also been the subject of one formal asymmetric synthesis …”