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Synfacts 2011(7): 0695-0695  
DOI: 10.1055/s-0030-1260489
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

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  
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Publication History

Publication Date:
17 June 2011 (online)

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Key words

alopecuridine - pinacol coupling - semipinacol rearrangement

Significance

(±)-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.

Comment

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.

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