Abstract
Carbohydrates have been utilized as starting materials for the synthesis of pyranopyrans, which are important building blocks for the total synthesis of polyethers and other natural products. This review focuses on the synthesis of pyranopyrans from carbohydrates, with emphasis on the stereoselective functionalization of sugars and on the methods used to construct additional rings onto a carbohydrate template. Anhydro sugars, deoxy sugars, lactones, glycals, glycosides and other derivatives of carbohydrates have been used as starting materials for the synthesis of natural products such as ansamycins, halichondrin B, okadaic acid, dactomelynes, thyrsiferol, and polyethers brevetoxin A, ciguatoxin, and brevisin. Methods for ring closure are covered and show a progression toward the increased use of metal-catalyzed processes.
Keywords: Carbohydrates, pyranopyrans, synthesis.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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