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Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis |
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| Authors: | Jack E. Baldwin Timothy D. W. Claridge Andrew J. Culshaw Florian A. Heupel Victor Lee David R. Spring Roger C. Whitehead Robert J. Boughtflower Ian M. Mutton Richard J. Upton |
| Abstract: | The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1 ), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels–Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH4. This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis. |
| Keywords: | Alkaloids Biomimetic synthesis Biosynthesis Diels– Alder reactions Manzamine |