Protecting Group Effects on the Total Syntheses of Several Classes of Natural Products

doi:10.6023/cjoc202406024

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (3): 1030-1039.DOI: 10.6023/cjoc202406024 Previous Articles Next Articles

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保护基效应对几类天然产物全合成的影响

易九州, 火亮, 陈金燕, 刘勐, 李辉林^*(), 厍学功^*()

兰州大学化学化工学院功能有机分子化学国家重点实验室兰州 730000

收稿日期:2024-06-18 修回日期:2024-08-01 发布日期:2024-09-18
基金资助:
国家自然科学基金(22231003); 国家自然科学基金(22071090); 国家自然科学基金(22171115)

Protecting Group Effects on the Total Syntheses of Several Classes of Natural Products

Jiuzhou Yi, Liang Huo, Jinyan Chen, Meng Liu, Huilin Li(), Xuegong She()

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Received:2024-06-18 Revised:2024-08-01 Published:2024-09-18
Contact: * E-mail: lihuilin@lzu.edu.cn; shexg@lzu.edu.cn
Supported by:
National Natural Science Foundation of China(22231003); National Natural Science Foundation of China(22071090); National Natural Science Foundation of China(22171115)

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Abstract

The proper utilization of protecting groups plays a pivotal role in the total synethesis of natural products. Recently, in the research on the total synthesis of several polycyclic natural products, it was found that, besides the masking effect on active functional groups, protecting groups brought many other effects to the chemical reactions and route evaluations of the synthesis in the following aspects including leading to unexpected skeletal rearrangement or reorganization, participating the designed reaction to produce unexpected byproducts, and affecting the outcome of stereoselectivity. In response to this, based on recent research cases on the complete synthesis of natural products, how to deal with the impact of protective group effects in specific situations is analyzed, and different solutions including replacing protective groups, directly applying by-products from protective groups, and abandoning the use of protective groups are proposed. These three solutions successfully tackled the probelms in the synthesis, and laid the foundation of final success on the total synthesis of the target molecules.

Key words: protecting group, natural product, total synthesis, skeletal rearrangement, side reaction

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Jiuzhou Yi, Liang Huo, Jinyan Chen, Meng Liu, Huilin Li, Xuegong She. Protecting Group Effects on the Total Syntheses of Several Classes of Natural Products[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 1030-1039.

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Fig. & Tab. 9

Figure 1. Structures of marsupellin-family sesquiterpenoids

Scheme 1. Two designed radical cyclization pathways

Scheme 2. Protecting group (PG) effect on the total syntheses of marsupellin-family sesquiterpenoids

Scheme 3. Structure and synthetic strategy of arborisidine

Scheme 4. PG effect on the total synthesis of arborisidine

Figure 2. Structures of gibberellic acid and pharbinilic acid

Scheme 5. PG effect on the total synthesis of pharbinillic acid

Scheme 6. Structure and synthetic strategy of pepluacetal

Scheme 7. PG effect on the total synthesis of pepluacetal

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保护基效应对几类天然产物全合成的影响

Protecting Group Effects on the Total Syntheses of Several Classes of Natural Products

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