ISSN:
0899-0042
Keywords:
macrocyclic spermidine alkaloids
;
stereoselective synthesis
;
absolute configuration
;
biogenesis
;
stereochemistry
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In this short review of several macrocyclic spermidine alkaloids, special consideration has been given to the correct determination of the absolute configuration at their chiral centers. The bases of interest are characterized by possessing a 13-membered macrocyclic lactam ring incorporating spermidine and either cinnammic or fatty acid precursorial units. In this context, the synthesis of some of these alkaloids is presented and the first total synthesis of optically pure (+)-(S)-viburnine, and (-)-(S)-celafurine is reported. Finally, a common initial step in biosynthesis starting with an enzyme-catalyzed Michael addition of spermidine to an α,β-unsaturated acid is proposed. Chirality 9:523-528, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
8 Ill.
Type of Medium:
Electronic Resource
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