A Cascade "Prins‐Pinacol‐Type Rearrangement and C4‐OBn Participation" on Carbohydrate Substrates: Synthesis of Bridged Tricyclic Ketals, Annulated Sugars and C2‐Branched Heptoses. Issue 51 (11th November 2016)

• Record Type: Journal Article
• Authors: Rajasekaran, Parasuraman; Singh, Govind Pratap; Hassam, Mohammad; Vankar, Yashwant D.
• Is Part Of: Chemistry. Volume 22:Issue 51(2016)
• Page Start: 18383
• Page End: 18387
• Publication Date: 2016-11-11
• Subjects: 1, 6-anhydro-heptopyronoses -- 2c-branched sugars -- annulated sugars -- cyclization -- rearrangement; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201604902
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A "Prins pinacol type rearrangement followed by C4‐OBn participation" in a cascade manner has been observed while probing the fate of carbocation in some carbohydrate derived homoallylic alcohols in the Prins reaction. This has led to an easy access to tetrahydrofuran‐fused bridged bicyclic ketals (or tetrahydrofuran‐fused 1, 6‐anhydro‐heptopyranose frameworks) which are further converted into some annulated sugars and C2‐branched heptoses. Abstract : Building bridges : A cascade Prins pinacol‐type rearrangement followed by C4–OBn participation on carbohydrate derived homoallylic alcohols, leading to tricyclic bridged ketals in one step. Further synthetic applications to form some annulated sugars and C2‐branched heptoses are reported.