Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A

doi:10.6023/cjoc202401017

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2350-2362.DOI: 10.6023/cjoc202401017 Previous Articles Next Articles

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抗生素Elansolid A简化衍生物的不对称全合成

杨帅^a^,^b, 吴杰^a^,^b, 汪亮亮^a^,^*()

a 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室昆明 650201
b 中国科学院大学北京 101408

收稿日期:2024-01-15 修回日期:2024-02-26 发布日期:2024-03-20
基金资助:
云南省高层次人才计划(Y93D321261); 中国科学院区域发展青年学者项目(E323521311); 及云南省科学技术厅(202305AH34005); 及云南省科学技术厅(202401AS070096)

Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A

Shuai Yang^a^,^b, Jie Wu^a^,^b, Liangliang Wang^a()

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201
b University of Chinese Academy of Sciences, Beijing 101408

Received:2024-01-15 Revised:2024-02-26 Published:2024-03-20
Contact: * E-mail: wangliangliang@mail.kib.ac.cn
Supported by:
High-Level Talent Program of Yunnan Province(Y93D321261); Regional Development Program for Young Scholars, Chinese Academy of Sciences (CAS)(E323521311); Science and Technology Department of Yunan Province(202305AH34005); Science and Technology Department of Yunan Province(202401AS070096)

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Abstract

Natural product elansolid A belongs to one type of polyketide macrolactone with promising antibiotic activity. Previously, the first total synthesis of elansolid A in 28 longest linear sequence (LLS) and 41 steps in total has been achieved. Herein, the simplified analog of elansolid A, featured with a cyclohexyl-fused 19-memebered macrolactone, was proposed, and its asymmetric total synthesis based on a convergent strategy and key reactions exemplified by desymmetric alcoholysis of anhydride, Pd-catalyzed Stille coupling, Suzuki-Miyaura coupling as well as Mukaiyama macrolactonization was finished.

Key words: asymmetric total synthesis, coupling reaction, simplified analog, elansolid A

Cite this article

Shuai Yang, Jie Wu, Liangliang Wang. Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2350-2362.

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Fig. & Tab. 6

Figure 1. Polyketide family of elansolids 1~3 and proposed simplified analog 4 of elansolid A1/A2

Scheme 1. Retrosynthetic plan for analog 4

Scheme 2. Synthesis of vinyl iodide fragment 5

Scheme 3. Assignment of absolute configuration of secondary alcohol by Mosher ester analysis based on the 1H NMR chemical shift

Scheme 4. Total synthesis of analog 4

Scheme 5. Total synthesis of C22-epi-4

References 16

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抗生素Elansolid A简化衍生物的不对称全合成

Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A

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Fig. & Tab. 6

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