The tethered nitrogen in natural products synthesis

Abstract

A variety of nitrogen-containing natural products, including aminosugars and aminocyclitols, have been synthesized by routes that feature the intramolecular delivery of a temporarily-tethered nitrogen nucleophile to an electrophilic site. This general tactic for amino group introduction frequently provides entropic advantages, as well as improved site selectivity and stereoselectivity, compared with the corresponding intermolecular approach. An occasional additional benefit is that the resulting cyclized products can be more easily manipulated toward the desired target than the corresponding free amino compounds. These aspects are illustrated in a discussion of several natural products syntheses from the author’s laboratory.

‘Help from without is often enfeebling in its effects, but help from within invariably invigorates’

Samuel Smiles, Self-Help, 1859

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