Synthetic Studies toward Natural Occurred Cyanolide A and Cocosolide

doi:10.6023/cjoc201904071

Abstract

Cyanolide A and cocosolide, two 16-membered dimeric macrolide xylopyranosides, were isolated from Guam and Papua New Guinea, respectively. Their fascinating structures and outstanding biological activities had attracted great attentions from chemists. The synthesis of cyanolide A and cocosolide is reviewed based on the construction methods of tetrahydropyran ring, which involves oxo-Michael addition reaction, oxo-carbenium cyclization and transition-metal catalyzed cyclization reactions.

Key words: cyanolide A, cocosolide, total synthesis, oxo-Michael addition, oxo-carbenium cyclization reaction, transition-metal catalyzed cyclization reaction

Cite this article

Zhang Liu, Zhang Mengfan, Qi Chenze, Yang Zhen. Synthetic Studies toward Natural Occurred Cyanolide A and Cocosolide[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3105-3113.

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Fig. & Tab. 14

Figure 1. Structures of cyanolide A and cocosolide

Scheme 1. Hong's first total synthesis of cyanolide A

Scheme 2. Reddy's synthesis of cyanolide A aglycone

Scheme 3. Pabbaraja's synthesis of cyanolide A aglycone

Scheme 4. Krische's total synthesis of cyanolide A

Scheme 5. Bates's total synthesis of cyanolide A

Scheme 6. Zhou's synthesis of cyanolide A aglycone

Scheme 7. Rychnovsky's first generation synthesis of cyanolide A aglycone

Scheme 8. Jennings's synthesis of cyanolide A aglycone

Scheme 9. Rychnovsky's second generation synthesis of cyanolide A

Scheme 10. She's total synthesis of cyanolide A

Scheme 11. Ye's total synthesis of cocosolide

Scheme 12. Synthesis of cyanolide A (1) and cocosolide (2)

Scheme 13. Synthetic plan for cocosolide (2)

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天然产物Cyanolide A和Cocosolide的合成研究进展