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Diversity‐Oriented Synthesis of Carbohydrate Scaffolds through the Prins Cyclization of Differently Protected d ‐Mannitol‐Derived Homoallylic Alcohols
Author(s) -
Dubbu Sateesh,
Vankar Yashwant D.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701172
Subject(s) - chemistry , prins reaction , furan , mannitol , carbohydrate , carbohydrate chemistry , allylic rearrangement , alcohol , organic chemistry , derivative (finance) , combinatorial chemistry , halide , catalysis , financial economics , economics
A diversity‐oriented synthesis of a variety of carbohydrate scaffolds, including sugar‐fused isochroman derivatives, bicyclic vinyl halide derivatives, fluorine‐substituted tetrahydropyrans, and a furan derivative, is reported. This was achieved through the Prins reaction of d ‐mannitol‐derived homoallylic alcohols in which the allylic alcohol bears a different protecting group, leading to structural variation in the products. Some of the products were also converted into more functionalized scaffolds of wider utility and of possible biological importance. Appropriate mechanisms have been proposed to account for the product formation.