Title Formal Total Synthesis of (+/-)-Lycojaponicumin C
Authors Zheng, Nan
Zhang, Lijie
Gong, Jianxian
Yang, Zhen
Affiliation Peking Univ, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China.
Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China.
Peking Univ, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China.
Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China.
Peking Univ, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China.
Yang, Z (reprint author), Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China.
Yang, Z (reprint author), Peking Univ, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China.
Yang, Z (reprint author), Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China.
Keywords CARBON QUATERNARY STEREOCENTERS
ASYMMETRIC TOTAL-SYNTHESIS
11-STEP TOTAL-SYNTHESIS
LYCOPODIUM ALKALOIDS
ENANTIOSELECTIVE SYNTHESIS
NATURAL-PRODUCTS
DIASTEREOSELECTIVE SYNTHESIS
RADICAL CYCLIZATION
(-)-MAOECRYSTAL V
MAOECRYSTAL V
Issue Date 2017
Publisher ORGANIC LETTERS
Citation ORGANIC LETTERS.2017,19(11),2921-2924.
Abstract The formal total synthesis of (+/-)-lycojaponicumin C has been accomplished. Key transformations include a Rh-catalyzed formal [3 + 2] cycloaddition reaction to construct the bicyclic [3.3.0] scaffold bearing two vicinal quaternary carbon centers, a stereoselective ?-hydroxyl directed Michael addition to introduce the vinyl group at a bulky position, and a late-stage ring-closing metathesis reaction to form the cyclohexanone ring.
URI http://hdl.handle.net/20.500.11897/472912
ISSN 1523-7060
DOI 10.1021/acs.orglett.7b01154
Indexed SCI(E)
Appears in Collections: 化学生物学与生物技术学院
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生命科学学院
生物有机与分子工程教育部重点实验室

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