共 27 条
Enantioselective total synthesis of the polycyclic guanidine-containing marine alkaloid (-)-batzelladine D
被引:57
作者:

Evans, P. Andrew
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机构:
Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

Qin, Jun
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h-index: 0
机构: Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

Robinson, John E.
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h-index: 0
机构: Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

Bazin, Berangere
论文数: 0 引用数: 0
h-index: 0
机构: Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
机构:
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词:
alkaloids;
asymmetric synthesis;
guanidines;
natural products;
total synthesis;
D O I:
10.1002/anie.200700840
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
(Chemical Equation Presented) Addressing the marine core: The enantioselective total synthesis of the polycyclic guanidine-containing marine alkaloid (-)-batzelladine D has been accomplished using a convergent 14-step reaction sequence (longest linear sequence) in 10% overall yield. The ability to accomplish the selective homolytic cleavage of an alkyl iodide in the presence of an azide circumvents the necessity for nitrogen-protecting groups. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
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页码:7417 / 7419
页数:3
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共 27 条
[1]
NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE
[J].
ALCARAZ, L
;
HARNETT, JJ
;
MIOSKOWSKI, C
;
MARTEL, JP
;
LEGALL, T
;
SHIN, DS
;
FALCK, JR
.
TETRAHEDRON LETTERS,
1994, 35 (30)
:5449-5452

ALCARAZ, L
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

HARNETT, JJ
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

MIOSKOWSKI, C
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

MARTEL, JP
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

LEGALL, T
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

SHIN, DS
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

FALCK, JR
论文数: 0 引用数: 0
h-index: 0
机构: CEA SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE
[2]
Diastereoselective [4+2] annulation of vinyl carbodiimides with N-alkyl imines.: Asymmetric synthetic access to the batzelladine alkaloids
[J].
Arnold, MA
;
Durón, SG
;
Gin, DY
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (19)
:6924-6925

Arnold, MA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Univ Illinois, Dept Chem, Urbana, IL 61801 USA

Durón, SG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Univ Illinois, Dept Chem, Urbana, IL 61801 USA

Gin, DY
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[3]
A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
[J].
Black, GP
;
Murphy, PJ
;
Walshe, NDA
.
TETRAHEDRON,
1998, 54 (32)
:9481-9488

Black, GP
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

Murphy, PJ
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

Walshe, NDA
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales
[4]
REGIOSELECTIVE SYNTHESIS OF N-SUBSTITUTED DIHYDROPYRIMIDIN-2(1H) OR (3H)-ONE
[J].
CHO, H
;
TAKEUCHI, Y
;
UEDA, M
;
MIZUNO, A
.
TETRAHEDRON LETTERS,
1988, 29 (42)
:5405-5408

CHO, H
论文数: 0 引用数: 0
h-index: 0

TAKEUCHI, Y
论文数: 0 引用数: 0
h-index: 0

UEDA, M
论文数: 0 引用数: 0
h-index: 0

MIZUNO, A
论文数: 0 引用数: 0
h-index: 0
[5]
Asymmetric total synthesis of batzelladine D
[J].
Cohen, F
;
Overman, LE
;
Sakata, SKL
.
ORGANIC LETTERS,
1999, 1 (13)
:2169-2172

Cohen, F
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Overman, LE
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Sakata, SKL
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
[6]
Studies towards the total synthesis of batzelladine A
[J].
Elliott, MC
;
Long, MS
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2004, 2 (14)
:2003-2011

Elliott, MC
论文数: 0 引用数: 0
h-index: 0
机构:
Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales

Long, MS
论文数: 0 引用数: 0
h-index: 0
机构:
Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales
[7]
Stereoselective construction of trans-disubstituted azabicycles using oxauracil as a novel free radical acceptor
[J].
Evans, PA
;
Manangan, T
;
Rheingold, AL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000, 122 (44)
:11009-11010

Evans, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA

Manangan, T
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA

Rheingold, AL
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA
[8]
Regioselective and enantiospecific rhodium-catalyzed allylic amination with thymine: synthesis of a new conformationally rigid nucleoside
[J].
Evans, PA
;
Lai, KW
;
Zhang, HR
;
Huffman, JC
.
CHEMICAL COMMUNICATIONS,
2006, (08)
:844-846

Evans, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Lai, KW
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Zhang, HR
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Huffman, JC
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[9]
Stereoselective construction of trans-disubstituted azabicycles using oxauracil as a novel free radical acceptor (vol 122, pg 11009, 2000)
[J].
Evans, PA
;
Manangan, T
;
Rheingold, AL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (47)
:16745-16745

Evans, PA
论文数: 0 引用数: 0
h-index: 0

Manangan, T
论文数: 0 引用数: 0
h-index: 0

Rheingold, AL
论文数: 0 引用数: 0
h-index: 0
[10]
Stereoselective construction of the azabicyclic core applicable to the biologically important polyguanidinium alkaloids batzelladine A and D using a free radical cyclization (vol 42, pg 6637, 2001)
[J].
Evans, PA
;
Manangan, T
.
TETRAHEDRON LETTERS,
2005, 46 (50)
:8811-8811

Evans, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Manangan, T
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA