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Absolute configuration of macrocyclic spermidine alkaloids

✍ Scribed by Katja Schultz; Paul Kuehne; Ursula A. Häusermann; Manfred Hesse

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
162 KB
Volume
9
Category
Article
ISSN
0899-0042

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✦ Synopsis

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 13membered 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 ␣,␤-unsaturated acid is proposed.

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