Divergent Total Synthesis of Euphoranginol C, Euphoranginone D,ent-Trachyloban-3 beta-ol,ent-Trachyloban-3-one, Excoecarin E, andent-16 alpha-Hydroxy-atisane-3-one
A divergent synthetic approach to biogenetically related diterpenoids such as ent-kauranes, ent-trachylobanes, ent-beyerane, and ent-atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]-octane moiety of ent-kaurane. The key reac...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 45; pp. 19919 - 19923 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
02.11.2020
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| Abstract | A divergent synthetic approach to biogenetically related diterpenoids such as ent-kauranes, ent-trachylobanes, ent-beyerane, and ent-atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]-octane moiety of ent-kaurane. The key reactions also include bioinspired nucleophilic cyclopropanation generating the [3.2.1.0(2,7)]-tricyclic core of ent-trachylobane and regioselective cyclopropane fragmentation furnishing ent-beyerane and ent-atisane through the nucleophilic attack and protonation of the cyclopropane ring. This strategy enables the asymmetric total syntheses of six diterpenoids from the commercially available geraniol. |
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| AbstractList | A divergent synthetic approach to biogenetically related diterpenoids such as ent-kauranes, ent-trachylobanes, ent-beyerane, and ent-atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]-octane moiety of ent-kaurane. The key reactions also include bioinspired nucleophilic cyclopropanation generating the [3.2.1.0(2,7)]-tricyclic core of ent-trachylobane and regioselective cyclopropane fragmentation furnishing ent-beyerane and ent-atisane through the nucleophilic attack and protonation of the cyclopropane ring. This strategy enables the asymmetric total syntheses of six diterpenoids from the commercially available geraniol. |
| Author | Fang, Liyuan Zhang, Jiao-Zhen Zheng, Hongbo Zhu, Ming-Zhu Liu, Xuyuan Wang, Xiao-ning Qiao, Ya-Nan Zong, Yan Xu, Ze-Jun Xu, Yuliang Lou, Hong-Xiang |
| Author_xml | – sequence: 1 givenname: Ze-Jun surname: Xu fullname: Xu, Ze-Jun organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 2 givenname: Yan surname: Zong fullname: Zong, Yan organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 3 givenname: Ya-Nan surname: Qiao fullname: Qiao, Ya-Nan organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 4 givenname: Jiao-Zhen surname: Zhang fullname: Zhang, Jiao-Zhen organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 5 givenname: Xuyuan surname: Liu fullname: Liu, Xuyuan organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 6 givenname: Ming-Zhu surname: Zhu fullname: Zhu, Ming-Zhu organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 7 givenname: Yuliang surname: Xu fullname: Xu, Yuliang organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 8 givenname: Hongbo surname: Zheng fullname: Zheng, Hongbo organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 9 givenname: Liyuan surname: Fang fullname: Fang, Liyuan organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 10 givenname: Xiao-ning surname: Wang fullname: Wang, Xiao-ning organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China – sequence: 11 givenname: Hong-Xiang surname: Lou fullname: Lou, Hong-Xiang email: louhongxiang@sdu.edu.cn organization: Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol MOE, 44 West Wenhua Rd, Jinan 250012, Peoples R China |
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| Keywords | terpenoids ATISANE-TYPE DITERPENOIDS REARRANGEMENTS cyclization PROTONATION natural products ENT-KAURANE DITERPENOIDS asymmetric synthesis CONSTRUCTION 1ST TOTAL-SYNTHESIS total synthesis ENANTIOSELECTIVE TOTAL-SYNTHESIS ALKALOIDS |
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| Title | Divergent Total Synthesis of Euphoranginol C, Euphoranginone D,ent-Trachyloban-3 beta-ol,ent-Trachyloban-3-one, Excoecarin E, andent-16 alpha-Hydroxy-atisane-3-one |
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