160910-86-1Relevant academic research and scientific papers
Stereochemical Control over Three Contiguous Stereogenic Centers in the Intramolecular Ene Reaction of Activated 1,6-Dienes. Application to the Synthesis of (±)-Methyl Cucurbate and (±)-Methyl Epijasmonate
Sarkar, Tarun K.,Ghorai, Binay K.,Nandy, Sandip K.,Mukherjee, Bireswar,Banerji, Asoke
, p. 6006 - 6011 (1997)
The influence of a protected alcohol group adjacent to the ene or enophile component on diastereoselectivity in both thermal and Lewis acid-catalyzed 5-(3,4) ene reactions of a series of 1,6-dienes 1-7 has been studied. The results indicate that its effect can be considerable, and in one example, with a gem-dimethyl group on the connecting chain and a large silyl protecting group on the hydroxyl, the diastereocontrol was almost perfect, with three stereogenic centers and one double bond geometry set up in one step, e.g., 4 → 10. This new finding was exploited in a synthesis of epijasmonoid natural products, (±)-methyl cucurbate (19) and (±)-methyl epijasmonate (18) starting from aldehyde 24, where the key step was a highly diastereocontrolled 5-(3,4) ene cyclization 23 → 22. 1 Indian Institute of Technology 2 BARC.
Intramolecular Alder ene approach to stereochemical control over three contiguous stereogenic centres: Synthesis of (±)-methyl cucurbate and (±)-methyl epijasmonate
Sarkar, Tarun K.,Ghorai, Binay K.,Banerji, Asoke
, p. 6907 - 6908 (2007/10/02)
The total synthesis of epijasmonoids, (±)-methyl cucurbate and (±)-methyl epijasmonate is described starting from aldehyde 14, where the key step is a highly stereocontrolled 5-(3,4) ene cyclization 17→18.
