Axisonitrile synthesis

We thank Dr. Roderick Bates, Chulalongkorn University, for drawing our attention to reference [113]which describes the synthesis of the unnatural enantiomer of axisonitrile-3. 

A total synthesis of the sesquiterpenoids (-)-axamide-4 1663 and (—)-axisonitrile-4 1664, affording both natural products, has been accomplished in eleven steps [1233]. From the view of a chemist, it is remarkable that both the isocyanide and its chemical precursor molecule formamide are naturally occurring. The transformation of (—)-axamide-4 into (—)-axisonitrile-4 is carried out with p-tosyl chloride in 94% yield. 

Tamura, K Nakazaki, A., and Kobayashi, S. (2009) StereocontroUed total synthesis of antimalarial (-F)-axisonitrile-3. Synlett. 2449-2452. 

Takahashi, K., Takeda, K and Honda, T. (2010) Efficient formal synthesis of ( )-axamide-l and (i)-axisonitrile-l via an intramolecular Hosomi-Sakurai reaction. Tetrahedron Lett., 51, 3542-3544. 

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