Research Progress on the Synthesis of Sesquiterpene Quinones and Hydroquinones Natural Products with Avarane Skeleton from Dysidea sp.

doi:10.6023/cjoc202304009

Abstract

Sesquiterpene quinones and hydroquinones obtained from the marine sponge Dysidea sp. with avarane skeleton are classified into three categories based on the differences of the bond connecting the quinone/hydroquinone unit and the sesquiterpene unit. The reported synthetic methods for these three types of natural products are reviewed in detail based on their key synthetic strategies with the aim of assisting in the synthesis of other natural products.

Key words: sesquiterpene quinone/hydroquinone, marine sponge Dysidea sp., avarane skeleton, synthetic strategy

Cite this article

Wen Xun, Liqing Jiang, Xiaolei Chen, Jingchun Wu, Feiyan Liang, Yinan Deng, Bo Xu. Research Progress on the Synthesis of Sesquiterpene Quinones and Hydroquinones Natural Products with Avarane Skeleton from Dysidea sp.[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4188-4212.

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Fig. & Tab. 30

Figure 1. Sesquiterpene quinones and hydroquinones with avarane skeleton from marine sponge Dysidea sp

Scheme 1. Biosynthetic hypothesis for dysideanone B and (+)-dysiherbols A~E

Scheme 2. Synthetic work (Ⅰ) of Lu?s group

Scheme 3. Synthetic work of Schmalz?s group

Scheme 4. Synthetic work of Tang?s group

Scheme 5. Synthetic work (Ⅱ) of Lu?s group

Scheme 6. Synthetic work (Ⅲ) of Lu?s group

Scheme 7. Synthetic work (Ⅳ) of Lu?s group

Scheme 8. Synthetic work of Lu?s group (Ⅴ)

Scheme 9. Synthetic work of Echavarren?s group

Scheme 10. Synthetic work of Liu?s group

Scheme 11. Synthetic work of Menche?s group

Scheme 12. Synthetic work of Shen?s group

Scheme 13. Synthetic work (I) of Qin?s group

Scheme 14. Synthetic work (Ⅵ) of Lu?s group

Scheme 15. Synthetic work (Ⅰ) of Katoh?s group

Scheme 16. Synthetic work (I) of Yang?s group

Scheme 17. Synthetic work (II) of Yang?s group

Scheme 18. Synthetic work (II) of Qin?s group

Scheme 19. Synthetic work (Ⅶ) of Lu?s group

Scheme 20. Synthetic work of Jana?s group

Scheme 21. Synthetic work of Sarma?s group

Scheme 22. Synthetic work of Hecht?s group

Scheme 23. Synthetic work of Wiemer?s group

Scheme 24. Synthetic work of Scott?s group

Scheme 25. Synthetic work of Terashima?s group

Scheme 26. Synthetic work of Anderson?s group

Scheme 27. Synthetic work (Ⅱ) of Katoh?s group

Scheme 28. Synthetic work of Theodorakis?s group

Scheme 29. Synthetic work (III) of Yang?s group

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具有avarane骨架结构的Dysidea属海绵来源的倍半萜醌/氢醌类天然产物的合成研究进展