The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. the enantioselective total synthesis of (-)-decarestrictine D.

被引：13

作者：

Pilli, RA ^{[1
]}

Victor, MM ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2001年 / 12卷 / 03期

关键词：

D O I：

10.1590/S0103-50532001000300009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of the intramolecular Nozaki-Hiyama-Kishi reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C4 and C5 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. The utility of this methodology has been demonstrated in the stereoselective total synthesis of (-)-decarestrictine D from 1,3-propanediol and polyhydroxybutyrate (PHB) in 13 steps and 6.3% overall yield.

引用

页码：373 / 385

页数：13

共 10 条

[1] Total synthesis of (-)-decarestrictine D through a stereoselective intramolecular Nozaki-Hiyama-Kishi reaction
Pilli, RA
Victor, MM
TETRAHEDRON LETTERS, 1998, 39 (25) : 4421 - 4424
[2] Stereoselectivity in the intramolecular Nozaki-Hiyama-Kishi reaction: influence of the substitution pattern and protecting groups in the construction of 10-membered lactones
Pilli, RA
Victor, MM
TETRAHEDRON LETTERS, 2002, 43 (15) : 2815 - 2818
[3] Synthesis of a 10-membered ring with eleutheside functionality by Nozaki-Hiyama-Kishi coupling
Sandova, Celso
Lopez-Perez, Jose L.
Bermejo, Francisco
TETRAHEDRON, 2007, 63 (47) : 11738 - 11747
[4] Total synthesis of (+)-herbarumin I via intermolecular Nozaki-Hiyama-Kishi reaction
Sabino, AA
Pilli, RA
TETRAHEDRON LETTERS, 2002, 43 (15) : 2819 - 2821
[5] The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in Enantioselective Catalytic Fluorinations and the Nozaki-Hiyama-Kishi Reaction
Deng, Qing-Hai
Wadepohl, Hubert
Gade, Lutz H.
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) : 14922 - 14928
[6] Intramolecular Nozaki-Hiyama-Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes
Dai, WM
Wu, AX
Hamaguchi, W
TETRAHEDRON LETTERS, 2001, 42 (25) : 4211 - 4214
[7] 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
[8] Total synthesis of LL-Z1640-2 utilizing a late-stage intramolecular Nozaki-Hiyama-Kishi reaction
LeClair, Christopher A.
Boxer, Matthew B.
Thomas, Craig J.
Maloney, David J.
TETRAHEDRON LETTERS, 2010, 51 (52) : 6852 - 6855
[9] 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
[10] 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

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