Journal
TETRAHEDRON
Volume 59, Issue 44, Pages 8757-8762Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.09.038
Keywords
(bis)indole alkaloids; Diels-Alder cycloaddition reactions; Diels-Alderases; chiral shift reagents; enantiomeric composition
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Reported here are two novel quasi-racemic (bis)indole alkaloids, cycloaplysinopsin A (5) and cycloaplysinopsin B (6), isolated from tropical Indo-Pacific (Comoros, Philippines) scleractinian corals of the family Dendrophylliidae. Although their structures suggest a Diels-Alder cycloaddition origin from aplysinopsin-type precursors, neither experiments, nor theory allowed us to clearly distinguish an enzymatic process with scarce enantioselection from the intrusion of an adventitious catalyst in the coral extracts, where the chiral environment caused a slight asymmetric induction. (C) 2003 Elsevier Ltd. All rights reserved.
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