Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation

被引：26

作者：

Wang, Bin ^{[1
]}

Xie, Yuanzhen ^{[1
]}

Yang, Qin

Zhang, Guozhu ^{[2
]}

Gu, Zhenhua ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 20期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; SESQUITERPENE LACTONE; KINETIC RESOLUTION; CARBONYL ADDITION; ASTERISCUNOLIDE-D; SOLANOECLEPIN; CHLORIDE; OLEFINS; (+)-ASTERISCANOLIDE; CYCLOPENTENONES;

D O I：

10.1021/acs.orglett.6b02767

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]hexane from diazo compound with a bicydo[2.2.1]heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki-Hiyama-Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde.

引用

页码：5388 / 5391

页数：4

共 44 条

[1] Total synthesis of LL-Z1640-2 utilizing a late-stage intramolecular Nozaki-Hiyama-Kishi reaction
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TETRAHEDRON LETTERS, 2010, 51 (52) : 6852 - 6855
[2] Synthesis of a 10-membered ring with eleutheside functionality by Nozaki-Hiyama-Kishi coupling
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[3] Total Synthesis of SacrolideA by Following a Nozaki-Hiyama-Kishi Macrocyclization Strategy
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ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (03) : 340 - 342
[4] Total synthesis of (+)-herbarumin I via intermolecular Nozaki-Hiyama-Kishi reaction
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Pilli, RA
TETRAHEDRON LETTERS, 2002, 43 (15) : 2819 - 2821
[5] Total synthesis of (-)-decarestrictine D through a stereoselective intramolecular Nozaki-Hiyama-Kishi reaction
Pilli, RA
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TETRAHEDRON LETTERS, 1998, 39 (25) : 4421 - 4424
[6] Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction
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Bryan, Christopher S.
Garson, Mary J.
Banwell, Martin G.
Ward, Jas S.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 460 - 470
[7] Protecting-Group Directed Stereoselective Intramolecular Nozaki-Hiyama-Kishi Reaction: A Concise and Efficient Total Synthesis of Amphidinolactone A
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Pattanayak, Manas R.
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (25) : 4775 - 4784
[8] Total Synthesis of Rhizopodin Enabled by a Late-Stage Oxazole Ring Formation Strategy
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ORGANIC LETTERS, 2024, 26 (41) : 8928 - 8933
[9] Intramolecular Nozaki-Hiyama-Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes
Dai, WM
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TETRAHEDRON LETTERS, 2001, 42 (25) : 4211 - 4214
[10] The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. the enantioselective total synthesis of (-)-decarestrictine D.
Pilli, RA
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (03) : 373 - 385

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