Stereoselective Total Syntheses of Paecilomycins E and F through a Protecting Group Directed Diastereoselective Intermolecular Nozaki-Hiyama-Kishi (NHK) Reaction

被引：27

作者：

Mohapatra, Debendra K. ^{[1
,2
]}

Reddy, D. Sai ^{[1
,2
]}

Mallampudi, N. Arjunreddy ^{[1
]}

Yadav, Jhillu S. ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India

[2] Acad Sci & Innovat Res, New Delhi 110001, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 23期

关键词：

Total synthesis; Natural products; C-C coupling; Dihydroxylation; Olefination; Cyclization; RESORCYLIC ACID LACTONES; SECONDARY ALCOHOLS; RADICICOL; HYPOTHEMYCIN; METABOLITES; LL-Z1640-2; OXIDATION; ALDEHYDES; COMPOUND; CHLORIDE;

D O I：

10.1002/ejoc.201402133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and concise approach to the total syntheses of paecilomycins E (1) and F (2) is described. A protecting group directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, a Julia-Kocienski olefination, a Sharpless asymmetric dihydroxylation, and De Brabander's lactonization protocol are used as the key steps.

引用

页码：5023 / 5032

页数：10

共 5 条

[1] Protecting-Group Directed Stereoselective Intramolecular Nozaki-Hiyama-Kishi Reaction: A Concise and Efficient Total Synthesis of Amphidinolactone A
Mohapatra, Debendra K.
Das, Pragna P.
Pattanayak, Manas R.
Gayatri, Gaddamanugu
Sastry, G. Narahari
Yadav, J. S.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (25) : 4775 - 4784
[2] The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues
Mohapatra, Debendra K.
Reddy, D. Sai
Mallampudi, N. Arjunreddy
Gaddam, Janardhan
Polepalli, Sowjanya
Jain, Nishant
Yadav, J. S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (47) : 9683 - 9695
[3] Total synthesis of (-)-decarestrictine D through a stereoselective intramolecular Nozaki-Hiyama-Kishi reaction
Pilli, RA
Victor, MM
TETRAHEDRON LETTERS, 1998, 39 (25) : 4421 - 4424
[4] Total synthesis of (+)-herbarumin I via intermolecular Nozaki-Hiyama-Kishi reaction
Sabino, AA
Pilli, RA
TETRAHEDRON LETTERS, 2002, 43 (15) : 2819 - 2821
[5] Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction
Bolte, Benoit
Basutto, Jose A.
Bryan, Christopher S.
Garson, Mary J.
Banwell, Martin G.
Ward, Jas S.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 460 - 470

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