Stereoselective Synthesis of the Halaven C14–C26 Fragment from D‐Quinic Acid: Crystallization‐Induced Diastereoselective Transformation of an α‐Methyl Nitrile1. (30th March 2015)

• Record Type: Journal Article
• Authors: Belanger, Francis; Chase, Charles E.; Endo, Atsushi; Fang, Francis G.; Li, Jing; Mathieu, Steven R.; Wilcoxen, Annie Z.; Zhang, Huiming
• Is Part Of: Angewandte Chemie. Volume 127:Number 17(2015)
• Page Start: 5197
• Page End: 5200
• Publication Date: 2015-03-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201501143
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Crystallization‐induced diastereoselective transformation (CIDT) of an α‐methyl nitrile completes an entirely non‐chromatographic synthesis of the halichondrin B C14–C26 stereochemical array. The requisite α‐methyl nitrile substrate is derived from <sc>D</sc>‐quinic acid through a series of substrate‐controlled stereoselective reactions via a number of crystalline intermediates that benefit from a rigid polycyclic template. Therefore, all four stereogenic centers in the Halaven C14–C26 fragment were derived from the single chiral source <sc>D</sc>‐quinic acid.</p> </abstract>