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. 2008 Oct 16;10(20):4449-52.
doi: 10.1021/ol8016947. Epub 2008 Sep 13.

Stereospecific total synthesis of somocystinamide A

Takashi L Suyama  1 , William H Gerwick
Affiliations

Stereospecific total synthesis of somocystinamide A

Takashi L Suyama et al. Org Lett. .

Abstract

The first total synthesis of somocystinamide A, a disulfide dimer with extremely labile enamide functional groups, was accomplished in a concise and stereospecific manner. Somocystinamide A is reported to possess exceptionally potent antiangiogenic and tumoricidal activities. The current work should enable further pharmacological investigation of this important natural product.

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Figures

Figure 1
Figure 1
Examples of disulfide-containing natural products.
Scheme 1
Scheme 1
Cross metathesis to 8
Scheme 2
Scheme 2
Synthesis of disulfide 15 (somocystinoic acid)
Scheme 3
Scheme 3
Possible mechanisms for enamide formation
Scheme 4
Scheme 4
Synthesis of somocystinamide A (1)
See this image and copyright information in PMC

References

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