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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Synthesis of ent-alantrypinone.

This paper presents a synthesis of ent-alantrypinone (ent-6), the enantiomer of a natural product produced by the fungus Penicillium thymicola. The synthesis revolves around the Li[Me(3)AlSPh]-promoted isomerization of iminobenzoxazine 33 to quinazolinone 34, an N-acyliminium ion cyclization that converts enamide 9 to bridged indole 35, and rearrangement of 35 to oxindole ent-6. Ancillary chemistry that involves thermal fragmentation of an iminobenzoxazine to a nitrile ylide and Me(2)AlSPh-mediated cyclization of oxime ether-ester 22 to pyrrolidinone 23 is also described.[1]


  1. Synthesis of ent-alantrypinone. Hart, D.J., Magomedov, N.A. J. Am. Chem. Soc. (2001) [Pubmed]
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