Studies on Synthesis of the C-1 to C-18 Fragment of Pamamycins 607 and 621A

被引：8

作者：

Ren Guobao ^{[1
]}

Wu Yikang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2010年 / 28卷 / 09期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; alcohol; antibiotic; cross metathesis; chiron; enantioselective synthesis; MACRODIOLIDES; ANTIBIOTICS;

D O I：

10.1002/cjoc.201090280

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Some efforts directed towards synthesis of the C-1 to C-18 fragment of natural antibiotic pamamycins 607 and 621A are disclosed. The nine stereogenic centers in the fragment were installed using a chiral auxiliary-induced asymmetric aldol reaction, a chiral building block derived from malic acid, or substrate chirality-induced asymmetric reduction of a ketone carbonyl group.

引用

页码：1651 / 1659

页数：9

共 28 条

[1] Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies
Anderson, JC
McDermott, BP
Griffin, EJ
[J]. TETRAHEDRON, 2000, 56 (44) : 8747 - 8767
[2] A shortcut to the smaller fragment of pamamycin-607
Bernsmann, H
Gruner, M
Fröhlich, R
Metz, P
[J]. TETRAHEDRON LETTERS, 2001, 42 (32) : 5377 - 5380
[3] Catalytic, asymmetric synthesis of the C1′-C10′ segment of pamamycin 621A
Calter, MA
Bi, FC
[J]. ORGANIC LETTERS, 2000, 2 (11) : 1529 - 1531
[4] Total synthesis of (-)-mucocin
Crimmins, Michael T.
Zhang, Yan
Diaz, Frank A.
[J]. ORGANIC LETTERS, 2006, 8 (11) : 2369 - 2372
[5] Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions
Crimmins, MT
Chaudhary, K
[J]. ORGANIC LETTERS, 2000, 2 (06) : 775 - 777
[6] Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry
Crimmins, MT
King, BW
Tabet, EA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7883 - 7884
[7] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
CHAPMAN, KT
CARREIRA, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) : 3560 - 3578
[8] A general sultone route to the pamamycin macrodiolides - Total synthesis of pamamycin-621A and pamamycin-635B
Fischer, P
Segovia, ABG
Gruner, M
Metz, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6231 - 6234
[9] The total synthesis of pamamycin-607. Part 2: Synthesis of the C6-C18 domain
Fraser, BH
Mulder, RJ
Perlmutter, P
[J]. TETRAHEDRON, 2006, 62 (12) : 2857 - 2867
[10] Synthesis of the C-1-C-28 ABCD unit of spongistatin 1
Gaunt, MJ
Jessiman, AS
Orsini, P
Tanner, HR
Hook, DF
Ley, SV
[J]. ORGANIC LETTERS, 2003, 5 (25) : 4819 - 4822

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