A de novo enantioselective total synthesis of (-)-laulimalide

被引：76

作者：

Nelson, SG ^{[1
]}

Cheung, WS ^{[1
]}

Kassick, AJ ^{[1
]}

Hilfiker, MA ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 46期

关键词：

D O I：

10.1021/ja028019k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective total synthesis of the naturally occurring anticancer agent (-)-laulimalide is described. The synthesis is characterized by extensive use of new reaction methodologies based on catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions and transformations of the derived enantioenriched β-lactones. The synthesis also incorporates a unique allenylstannane glycal acetate alkylation and chemoselective ring-closing metathesis reaction. Copyright © 2002 American Chemical Society.

引用

页码：13654 / 13655

页数：2

共 25 条

[1] BROWN HC, 1979, SYNTHESIS-STUTTGART, P704
[2] ASYMMETRIC METHALLYLBORATION OF PROCHIRAL ALDEHYDES WITH METHALLYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS OF 2-METHYL-1-ALKEN-4-OLS IN GREATER-THAN 90-PERCENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
PERUMAL, PT
[J]. TETRAHEDRON LETTERS, 1984, 25 (45) : 5111 - 5114
[3] THE E/Z GEOMETRY OF THE ENOLATE COMPONENT DETERMINES FACE SELECTION OF THE ALDEHYDE COMPONENT IN CHIRAL DIAZABOROLIDINE-DIRECTED ENANTIOSELECTIVE ALDOL COUPLING
COREY, EJ
LEE, DH
[J]. TETRAHEDRON LETTERS, 1993, 34 (11) : 1737 - 1740
[4] LAULIMALIDES - NEW POTENT CYTO-TOXIC MACROLIDES FROM A MARINE SPONGE AND A NUDIBRANCH PREDATOR
CORLEY, DG
HERB, R
MOORE, RE
SCHEUER, PJ
PAUL, VJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3644 - 3646
[5] Asymmetric total synthesis of (-)-laulimalide: Exploiting the asymmetric glycolate alkylation reaction
Crimmins, MT
Stanton, MG
Allwein, SP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5958 - 5959
[6] LEWIS ACID-CATALYZED CYCLOCONDENSATIONS OF FUNCTIONALIZED DIENES WITH ALDEHYDES
DANISHEFSKY, S
KERWIN, JF
KOBAYASHI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) : 358 - 360
[7] Macrocyclization via allyl transfer: Total synthesis of laulimalide
Enev, VS
Kaehlig, H
Mulzer, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) : 10764 - 10765
[8] Application of complex aldol reactions to the total synthesis of phorboxazole B
Evans, DA
Fitch, DM
Smith, TE
Cee, VJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) : 10033 - 10046
[9] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[10] Total synthesis of (-)-laulimalide
Ghosh, AK
Wang, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) : 11027 - 11028

← 1 2 3 →