A Cascade “Prins‐Pinacol‐Type Rearrangement and C4‐OBn Participation” on Carbohydrate Substrates: Synthesis of Bridged Tricyclic Ketals,Annulated Sugars and C2‐Branched Heptoses |
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| Authors: | Parasuraman Rajasekaran Dr Govind Pratap Singh Dr Mohammad Hassam Prof?Dr Yashwant D Vankar |
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| Institution: | Department of Chemistry, Indian Institute of Technology, Kanpur, India |
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| 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. |
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| Keywords: | 1 6-anhydro-heptopyronoses 2c-branched sugars annulated sugars cyclization rearrangement |
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