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Access to an anti , syn ‐1,5,7‐Triol by Configuration‐Encoded 1,5‐Polyol Synthesis: The C15–C25 Fragment of Tetrafibricin
Author(s) -
Friedrich Ryan M.,
Friestad Gregory K.
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.201700373
Subject(s) - triol , chemistry , conjugate , polyol , intramolecular force , stereochemistry , moiety , diol , combinatorial chemistry , organic chemistry , polyurethane , mathematical analysis , mathematics
A configuration‐encoded strategy provides unambiguous stereocontrol in an efficient synthesis of 1,5‐polyols. To access the anti , syn ‐1,5,7‐triol moiety of the C15–C25 fragment of tetrafibricin, a fibrinogen receptor antagonist, a strategy is introduced, which sequences the 1,5‐polyol synthesis with selective desilylation and diastereoselective intramolecular conjugate addition. For tetrafibricin, assembly of the C15–C25 anti ‐1,5‐diol in five steps is followed by the conjugate addition to introduce a syn ‐1,3‐diol to complete the anti , syn ‐1,5,7‐triol unit and to provide the functionality and stereochemistry required for tetrafibricin synthesis.