83333-58-8Relevant academic research and scientific papers
A model study for the total synthesis of (±)-scopadulin: Stereoselective construction of the A/B ring system with desired functionalities
Abdur Rahman,Ohno, Hiroaki,Yoshino, Hitoshi,Satoh, Norifumi,Tsukaguchi, Mahoto,Murakami, Kazuo,Iwata, Chuzo,Maezaki, Naoyoshi,Tanaka, Tetsuaki
, p. 127 - 134 (2007/10/03)
A model study toward the total synthesis of (±)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA-BOMCl, and conversion of the cyano group into a methyl group.
Efficient one-step conversion of primary aliphatic amines into primary alcohols: Application to a model study for the total synthesis of (±)-scopadulin
Rahman, S. M. Abdur,Ohno, Hiroaki,Maezaki, Naoyoshi,Iwata, Chuzo,Tanaka, Tetsuaki
, p. 2893 - 2895 (2007/10/03)
Treatment of primary aliphatic amines with KOH in diethylene glycol at 210°C gives primary alcohols directly in good yields. A synthetic application to a model study of (±)-scopadulin is also described.
Cyclopentene and Cyclohexene Annulation via Copper-Catalyzed Conjugate Addition of Acetal-Containing Grignard Reagents
Bal, Swati A.,Marfat, Anthony,Helquist, Paul
, p. 5045 - 5050 (2007/10/02)
The Grignard reagents 2 derived from 2-(bromoethyl)- and 2-(3-chloropropyl)-1,3-dioxolane undergo conjugate addition to a number of α,β-unstaurated ketones in the presence of a catalytic amount of a cuprous salt.The resulting keto acetals, upon treatment with hydrochloric acid, undergo sequential hydrolysis, intramolecular aldol condensation, and dehydration to give cyclopentene and cyclohexene annulation products.The entire series of reactions, starting with the conjugate addition, may be performed as a one flask experiment leading to direct formation of thecyclization products.The Grignard reagents may also be alkylated with epoxides or acylated with an acid chloride to give intermediates that may be converted into cyclic products by pathways related to those above.
