Synthesis of the branched C-glycoside substructure of altromycin B

被引：48

作者：

Koo, B ^{[1
]}

McDonald, FE ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 17期

关键词：

D O I：

10.1021/ol050975u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).

引用

页码：3621 / 3624

页数：4

共 39 条

[11] ALTROMYCIN-B THREADS THE DNA HELIX INTERACTING WITH BOTH THE MAJOR AND THE MINOR GROOVES TO POSITION ITSELF FOR SITE-DIRECTED ALKYLATION OF GUANINE-N7
HANSEN, M
HURLEY, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) : 2421 - 2429
[12] HEDAMYCIN INTERCALATES THE DNA HELIX AND, THROUGH CARBOHYDRATE-MEDIATED RECOGNITION IN THE MINOR-GROOVE, DIRECTS N7-ALKYLATION OF GUANINE IN THE MAJOR GROOVE IN A SEQUENCE-SPECIFIC MANNER
HANSEN, M
YUN, S
HURLEY, L
[J]. CHEMISTRY & BIOLOGY, 1995, 2 (04): : 229 - 240
[13] A novel reaction for annulation onto α,β-unsaturated ketones:: W(CO)5•L promoted exo- and endo-selective cyclizations of ω-acetylenic silyl enol ethers prepared by 1,4-addition of propargyl malonate to enones
Iwasawa, N
Maeyama, K
Kusama, H
[J]. ORGANIC LETTERS, 2001, 3 (24) : 3871 - 3873
[14] ALTROMYCINS, NOVEL PLURAMYCIN-LIKE ANTIBIOTICS .1. TAXONOMY OF THE PRODUCING ORGANISM, FERMENTATION AND ANTIBACTERIAL ACTIVITY
JACKSON, M
KARWOWSKI, JP
THERIAULT, RJ
HARDY, DJ
SWANSON, SJ
BARLOW, GJ
TILLIS, PM
MCALPINE, JB
[J]. JOURNAL OF ANTIBIOTICS, 1990, 43 (03) : 223 - 228
[15] Kamenecka TM, 2001, CHEM-EUR J, V7, P41, DOI 10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO
[16] 2-D
[17] KAPADIA VFS, 1994, J ORG CHEM, V12, P1047
[18] CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
VANNIEUWENHZE, MS
SHARPLESS, KB
[J]. CHEMICAL REVIEWS, 1994, 94 (08) : 2483 - 2547
[19] W(CO)5-amine catalyzed exo- and endo-selective cyclizations of ω-alkynyl silyl enol ethers:: A highly useful method for the construction of polycyclic compounds
Kusama, H
Yamabe, H
Iwasawa, N
[J]. ORGANIC LETTERS, 2002, 4 (15) : 2569 - 2571
[20] 3-STANNYLCYCLOBUTENEDIONES AS NUCLEOPHILIC CYCLOBUTENEDIONE EQUIVALENTS - SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES AND CYCLOBUTENEDIONE MONOACETALS AND THE BENEFICIAL EFFECT OF CATALYTIC COPPER IODIDE ON THE STILLE REACTION
LIEBESKIND, LS
FENGL, RW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5359 - 5364

← 1 2 3 4 →