The synthesis of an exhaustively stereodiversified library of cis-1,5 enediols by silyl-tethered ring-closing metathesis

被引：38

作者：

Harrison, BA ^{[1
]}

Verdine, GL ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 14期

关键词：

D O I：

10.1021/ol0159569

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] This report describes the parallel synthesis of all 16 stereoisomers of the cis-1,5 enediol module 1, Compounds 1 derive from 2 by silicon tethered ring-closing metathesis. Such libraries of stereodiversified ligands provide a unique approach to ligand discovery that employs exhaustive searching of conformational space.

引用

页码：2157 / 2159

页数：3

共 31 条

[1] The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].

Abiko, A ;

Liu, JF ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587

[2]

Annis DA, 1998, ANGEW CHEM INT EDIT, V37, P1907, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1907::AID-ANIE1907>3.0.CO

[3]

2-A

[4] Molecular recognition of protein-ligand complexes: Applications to drug design [J].

Babine, RE ;

Bender, SL .

CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472

[5] Formation of dissymmetric eight-membered silalketals by ring-closing metathesis and their conversion to spiroketals [J].

Boiteau, JG ;

Van de Weghe, P ;

Eustache, J .

TETRAHEDRON LETTERS, 2001, 42 (02) :239-242

[6] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[7] TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453

[8] Temporary silicon-tethered ring-closing metathesis approach to C2-symmetrical 1,4-diols:: Asymmetric synthesis of D-altritol [J].

Evans, PA ;

Murthy, VS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6768-6769

[9] Stereochemical implications on diversity in β-turn peptidomimetic libraries [J].

Feng, YB ;

Pattarawarapan, M ;

Wang, ZC ;

Burgess, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9175-9177

[10] Ruthenium carbene complexes with N,N′-bis(mesityl) imidazol-2-ylidene ligands:: RCM catalysts of extended scope [J].

Fürstner, A ;

Thiel, OR ;

Ackermann, L ;

Schanz, HJ ;

Nolan, SP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2204-2207

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