Synthesis of (±)-Alopecuridine

doi:10.1055/s-0030-1260489

Synfacts 2011(7): 0695-0695
DOI: 10.1055/s-0030-1260489

Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Alopecuridine

Contributor(s):Steven V. Ley, Catherine F. Carter

X.-M. Zhang, Y.-Q. Tu*, F.-M. Zhang, H. Shao, X. Meng
Lanzhou University, P. R. of China
Total Synthesis of (±)-Alopecuridine and Its Biomimetic Transformation into (±)-Sieboldine A
Angew. Chem. Int. Ed. 2011, 50: 3916-3919

Abstract

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Key words

alopecuridine - pinacol coupling - semipinacol rearrangement

Significance

<P>(±)-Alopecuridine A is a Lycopodium alkaloid that is a biological precursor for the significantly cytotoxic (±)-sieboline A. The first total synthesis is achieved here in 13 steps, followed by the conversion into (±)-sieboline A that validates the biogenetic pathway.</P>

Comment

<P>Compounds E and F were obtained as an inseparable mixture of diastereoisomers that were subjected to semipinacol rearrangement conditions. This generated a mixture of diastereomers that could then be separated by chromatography to give the desired intermediate G in 45% yield. The tricyclic core J was synthesized with a samarium iodide mediated coupling.</P>

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