Synthesis of e nt-Alantrypinone

DJ Hart, NA Magomedov

文献索引：Hart; Magomedov Journal of the American Chemical Society, 2001 , vol. 123, # 25 p. 5892 - 5899

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被引用次数: 57

摘要

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 [Me3AlSPh]-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 ...