共 22 条
The solution to a deep stereochemical conundrum: Studies toward the tetrahydroisoquinoline alkaloids
被引:23
作者:

Chan, C
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Zheng, SP
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Zhou, BS
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Guo, J
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Heid, RM
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Wright, BJD
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA

Danishefsky, S
论文数: 0 引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA Columbia Univ, Dept Chem, New York, NY 10027 USA
机构:
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词:
antitumor agents;
asymmetric synthesis;
Mannich cyclization;
natural products;
total synthesis;
D O I:
10.1002/anie.200503982
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
(Chemical Equation Presented) Facile construction of subunits 1 and 2 allowed the rapid assembly of the pentacyclic ring system 3 of the cytotoxic tetrahydroisoquinoline alkaloids. A surprising participation reaction was discovered, which necessitated revision of the stereochemical assignments of key intermediates en route to 3. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1749 / 1754
页数:6
相关论文
共 22 条
[1]
PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
[J].
BURK, MJ
;
FEASTER, JE
;
NUGENT, WA
;
HARLOW, RL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1993, 115 (22)
:10125-10138

BURK, MJ
论文数: 0 引用数: 0
h-index: 0
机构:
DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880

FEASTER, JE
论文数: 0 引用数: 0
h-index: 0
机构:
DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880

NUGENT, WA
论文数: 0 引用数: 0
h-index: 0
机构:
DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880

HARLOW, RL
论文数: 0 引用数: 0
h-index: 0
机构:
DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880
[2]
REGIOSELECTIVE AZIDE OPENING OF 2,3-EPOXY ALCOHOLS BY [TI(O-I-PR)2(N3)2] - SYNTHESIS OF ALPHA-AMINO-ACIDS
[J].
CARON, M
;
CARLIER, PR
;
SHARPLESS, KB
.
JOURNAL OF ORGANIC CHEMISTRY,
1988, 53 (21)
:5185-5187

CARON, M
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

CARLIER, PR
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

SHARPLESS, KB
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139
[3]
Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control
[J].
Chan, C
;
Heid, R
;
Zheng, SP
;
Guo, JS
;
Zhou, BS
;
Furuuchi, T
;
Danishefsky, SJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (13)
:4596-4598

Chan, C
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Heid, R
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Zheng, SP
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Guo, JS
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Zhou, BS
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Furuuchi, T
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA

Danishefsky, SJ
论文数: 0 引用数: 0
h-index: 0
机构: Columbia Univ, Dept Chem, New York, NY 10027 USA
[4]
Total synthesis of ecteinascidin 743
[J].
Chen, JC
;
Chen, XC
;
Bois-Choussy, M
;
Zhu, JP
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (01)
:87-89

Chen, JC
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Chen, XC
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Bois-Choussy, M
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Zhu, JP
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[5]
Enantioselective total synthesis of ecteinascidin 743
[J].
Corey, EJ
;
Gin, DY
;
Kania, RS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1996, 118 (38)
:9202-9203

Corey, EJ
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge

Gin, DY
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge

Kania, RS
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge
[6]
Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B
[J].
Cuevas, C
;
Pérez, M
;
Martín, MJ
;
Chicharro, JL
;
Fernández-Rivas, C
;
Flores, M
;
Francesch, A
;
Gallego, P
;
Zarzuelo, M
;
de la Calle, F
;
García, J
;
Polanco, C
;
Rodríguez, I
;
Manzanares, I
.
ORGANIC LETTERS,
2000, 2 (16)
:2545-2548

Cuevas, C
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Pérez, M
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Martín, MJ
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Chicharro, JL
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Fernández-Rivas, C
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Flores, M
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Francesch, A
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Gallego, P
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Zarzuelo, M
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

de la Calle, F
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

García, J
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Polanco, C
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Rodríguez, I
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain

Manzanares, I
论文数: 0 引用数: 0
h-index: 0
机构:
Pharma Mar, Madrid 28760, Spain Pharma Mar, Madrid 28760, Spain
[7]
Total synthesis of ecteinascidin 743
[J].
Endo, A
;
Yanagisawa, A
;
Abe, M
;
Tohma, S
;
Kan, T
;
Fukuyama, T
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002, 124 (23)
:6552-6554

Endo, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan

Yanagisawa, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan

Abe, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan

Tohma, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan

Kan, T
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan

Fukuyama, T
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Cooperat,JST,Bunkyo Ku, Tokyo 1130033, Japan
[8]
CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
[J].
GAO, Y
;
HANSON, RM
;
KLUNDER, JM
;
KO, SY
;
MASAMUNE, H
;
SHARPLESS, KB
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1987, 109 (19)
:5765-5780

GAO, Y
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

HANSON, RM
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

KLUNDER, JM
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

KO, SY
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

MASAMUNE, H
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

SHARPLESS, KB
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139
[9]
PALLADIUM-CATALYZED VINYLATION OF ORGANIC HALIDES UNDER SOLID LIQUID-PHASE TRANSFER CONDITIONS
[J].
JEFFERY, T
.
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1984, (19)
:1287-1289

JEFFERY, T
论文数: 0 引用数: 0
h-index: 0
[10]
Asymmetric total syntheses of (-)-jorumycin, (-)-renieramycin G, 3-epi jorumycin, and 3-epi-renieramycin G
[J].
Lane, JW
;
Chen, YY
;
Williams, RM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (36)
:12684-12690

Lane, JW
论文数: 0 引用数: 0
h-index: 0
机构: Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

Chen, YY
论文数: 0 引用数: 0
h-index: 0
机构: Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

Williams, RM
论文数: 0 引用数: 0
h-index: 0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA