Access to an anti, syn‐1, 5, 7‐Triol by Configuration‐Encoded 1, 5‐Polyol Synthesis: The C15–C25 Fragment of Tetrafibricin. Issue 14 (13th April 2017)

• Record Type: Journal Article
• Authors: Friedrich, Ryan M.; Friestad, Gregory K.
• Is Part Of: European journal of organic chemistry. Issue 14(2017)
• Page Start: 1961
• Page End: 1964
• Publication Date: 2017-04-13
• Subjects: Natural products -- Asymmetric synthesis -- Olefination -- Alcohols; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700373
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 : A strategy that sequences configuration‐encoded 1, 5‐polyol synthesis with diastereoselective intramolecular conjugate addition accesses the C15–C25 anti, syn ‐1, 5, 7‐triol of tetrafibricin, a fibrinogen receptor antagonist. Assembly of the anti ‐1, 5‐diol is followed by conjugate addition to introduce a syn ‐1, 3‐diol to provide the functionality and stereochemistry required for tetrafibricin synthesis.