A new total synthesis of the heptacyclic alkaloid (�)-communesin F has been achieved. Key reactions include an intramolecular Heck cyclization of a tetrasubstituted alkene to generate a tetracycle with a quaternary carbon center, an intramolecular reductive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework along with the southern aminal, a stereoselective lactam C-allylation to introduce the second quaternary carbon center, and an azide reduction-N-Boc-lactam opening cascade leading to the northern aminal. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/4004_mitten.jpg' alt='' />

Total synthesis of the polycyclic fungal alkaloid ([plusmn])-Communesin F

239th National Meeting (2010)

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