A concise total synthesis of the notoamides C and D

被引:76
作者
Grubbs, Alan W.
Artman, Gerald D., III
Tsukamoto, Sachiko
Williams, Robert M. [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
[3] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan
关键词
biomimetic synthesis; indoles; natural products; oxidation; pinacols;
D O I
10.1002/anie.200604377
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A unique oxidation: The first total synthesis of the prenylated indole alkaloids notoamide C and D was accomplished by using a biomimetic oxidation pathway. Oxidation of the putative biosynthetic precursor 1 was achieved in a one-pot reaction to afford notoamide C, its epimer, and notoamide D (see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2257 / 2261
页数:5
相关论文
共 45 条
[1]   Concise synthesis of the core bicyclo[2.2.2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids [J].
Adams, LA ;
Gray, CR ;
Williams, RM .
TETRAHEDRON LETTERS, 2004, 45 (23) :4489-4493
[2]   A concise synthesis of d,l-brevianamide B via a biomimetically-inspired IMDA construction [J].
Adams, Luke A. ;
Valente, Meriah W. N. ;
Williams, Robert M. .
TETRAHEDRON, 2006, 62 (22) :5195-5200
[3]  
[Anonymous], 2005, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200461864
[4]   Enantioselective total synthesis of avrainvillamide and the stephacidins [J].
Baran, Phil S. ;
Hafensteiner, Benjamin D. ;
Ambhaikar, Narendra B. ;
Guerrero, Carlos A. ;
Gallagher, John D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8678-8693
[5]   Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B [J].
Baran, PS ;
Guerrero, CA ;
Hafensteiner, BD ;
Ambhaikar, NB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3892-3895
[6]   Short, enantioselective total synthesis of Stephacidin A [J].
Baran, PS ;
Guerrero, CA ;
Ambhaikar, NB ;
Hafensteiner, BD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :606-609
[7]  
BARAN PS, 2005, ANGEW CHEM, V117, P3960
[8]   NEW PARAHERQUAMIDE ANTIBIOTICS WITH ANTHELMINTIC ACTIVITY [J].
BLANCHFLOWER, SE ;
BANKS, RM ;
EVERETT, JR ;
MANGER, BR ;
READING, C .
JOURNAL OF ANTIBIOTICS, 1991, 44 (05) :492-497
[9]   Stereocontrolled total synthesis of (+)-paraherquamide B [J].
Cushing, TD ;
SanzCervera, JF ;
Williams, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (03) :557-579
[10]  
CUTRONE JQ, 2001, Patent No. 6291461