Access to an anti,syn-1,5,7-Triol by Configuration-Encoded 1,5-Polyol Synthesis: The C15–C25 Fragment of Tetrafibricin.

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. [ABSTRACT FROM AUTHOR]