Recent Progresses in the Synthesis of Solanoeclepin A

doi:10.6023/cjoc201904055

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2759-2770.DOI: 10.6023/cjoc201904055 Previous Articles Next Articles

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四降三萜solanoeclepin A的合成研究进展

孙茂^a, 邱发洋^d^*(), 李卫东^b^c^*()

^a 安顺市人民医院药学实验室安顺 561000
^b 重庆大学药学院天然产物全合成与创新药物研究重庆市重点实验室重庆 401331
^c 西南交通大学生命科学与工程学院成都 610031
^d 中国科学院广州生物医药与健康研究院广州 510530

收稿日期:2019-04-23 修回日期:2019-05-13 发布日期:2019-06-03
通讯作者: 邱发洋,李卫东 E-mail:qiu_fayang@gibh.ac.cn;wdli@cqu.edu.cn
基金资助:
国家自然科学基金资助项目(21672030)

Recent Progresses in the Synthesis of Solanoeclepin A

Sun Mao^a, Qiu Fayang^d^*(), Li Wei-Dong^b^c^*()

^a Pharmaceutical Laboratory, An Shun City People’s Hospital, Anshun 561000;
^b Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 40133
^c School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
^d Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530

Received:2019-04-23 Revised:2019-05-13 Published:2019-06-03
Contact: Qiu Fayang,Li Wei-Dong E-mail:qiu_fayang@gibh.ac.cn;wdli@cqu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(21672030)

Solanoeclepin A, first isolated from potato roots (Solanaceae Juss.) by Mulder et al., is an highly active hatching stimulant (0.3 g per hectare) of potato cyst nematode (PCN, Globodera rostochiensis and G. pallida) which causes severe damage to potato crops. Its complex chemical structure belongs to a rearranged tetranortriterpene and possesses extremely unique skeleton. Based on the known general biosynthesis of tetranortriterpenoids and Prof. Corey’s biomimetic synthesis of glycinoeclepin, a plausible biosynthetic pathway of solanoeclepin A is proposed. A schematic review on the synthetic studies towards solanoeclepin A is provided.

Key words: solanoeclepin A, tetranortriterpene, natural product, total synthesis

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Sun Mao, Qiu Fayang, Li Wei-Dong. Recent Progresses in the Synthesis of Solanoeclepin A[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2759-2770.

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Fig. & Tab. 25

Figure 1. Structures of azadirachtin and micrandilactone A

Figure 2. Structures of glycinoeclepin and solanoeclepin A

Scheme 1. Corey’s biosynthetic route of gycinoeclepin

Scheme 2. Proposed major biosynthesis routes of solanoeclepin A

Figure 3. Tanino and Miyashitakey’s key synthetic strategy

Scheme 3. Synthesis of DEFG ring system

Scheme 4. Construction of ABC ring system via intramolecular Diels-Alder reaction

Figure 4. Hiemstra’s key synthetic strategy

Scheme 5. Hiemstra’s formal synthesis of solanoeclepin A

Figure 5. Hiemstra's key synthetic strategy

Scheme 6. Hiemstra’s synthesis of the ABC ring system of solanoeclepin A

Scheme 7. Construction of AB ring system via iodoetherification

Scheme 8. Isobe’s synthesis of the ABC ring system of solanoeclepin A

Figure 6. Adachi and Nishikawa's key synthetic strategy

Scheme 9. Adachi and Nishikawa’s synthesis of the ABC ring system of solanoeclepin A

Figure 7. Li’s key synthetic strategy

Scheme 10. Construction of ABC ring system via Diels-Alder reaction

Figure 8. Isobe's key synthetic strategy

Scheme 11. Cobalt-mediated Hosomi-Sakurai type cyclization

Scheme 12. SmI2-mediated 4-exo-trig intramolecular cyclization

Scheme 13. Adachi and Nishikawa’s synthesis of DEF ringsystem

Figure 9. Li and Qiu’s key synthetic strategy

Scheme 14. Li and Qiu’s synthesis of DEF ring system

Scheme 15. Li and Qiu’s synthesis of DEFG ring system

Scheme 16. Schematic summary of the synthetic studies towards solanoeclepin A

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四降三萜solanoeclepin A的合成研究进展

Recent Progresses in the Synthesis of Solanoeclepin A

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Fig. & Tab. 25

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