A Short and Efficient Enantioselective Synthesis of (+)‐(2S, 3S, 5S)‐epi‐Muscarine. Issue 21 (5th June 2020)

• Record Type: Journal Article
• Authors: Gehlawat, Anju; Prakash, Ranjana; Kumar Pandey, Satyendra
• Is Part Of: ChemistrySelect. Volume 5:Issue 21(2020)
• Page Start: 6373
• Page End: 6375
• Publication Date: 2020-06-05
• Subjects: Alkaloids -- Asymmetric synthesis -- Intramolecular SN2 cyclization -- Muscarine -- Sharpless AD; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202001598
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A short, efficient and novel enantioselective general approach for the synthesis of muscarine alkaloid and its application to the asymmetric synthesis of epi ‐muscarine from readily available ( R )‐PMB glycidyl ether as starting material is described. Key transformations include Sharpless asymmetric dihydroxylation (AD), regioselective epoxide ring opening and intramolecular SN 2 cyclization. Abstract : An efficient and novel general method for asymmetric synthesis of muscarine alkaloids and its application to the total synthesis of (+)‐ epi ‐muscarine from ( R )‐PMB glycidyl ether as starting material is presented. Key transformations include Sharpless asymmetric dihydroxylation (AD), regioselective epoxide ring opening and intramolecular SN 2 cyclization.