Enantioselective total synthesis of (-)-flustramines A, B and (-)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence

被引:56
作者
Kawasaki, T [1 ]
Shinada, M [1 ]
Kamimura, D [1 ]
Ohzono, M [1 ]
Ogawa, A [1 ]
机构
[1] Mieji Pharmaceut Univ, Tokyo 2048588, Japan
关键词
D O I
10.1039/b512485a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The concise total synthesis of marine alkaloids, (-)-flustramines A and B, and (-)-flustramides A and B has been achieved through the domino olefination/isomerization/Claisen rearrangement (OIC) for highly enantioselective construction of the asymmetric quaternary carbon center and the chemoselective reduction-cyclization (RC) for pyrrolidine formation as key steps.
引用
收藏
页码:420 / 422
页数:3
相关论文
共 38 条
[1]  
Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9
[2]   Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].
Austin, JF ;
Kim, SG ;
Sinz, CJ ;
Xiao, WJ ;
MacMillan, DWC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487
[3]   THE TOTAL SYNTHESIS OF (-)-DIHYDROASZONALENIN AND THE STEREOCHEMISTRY OF ASZONALENIN [J].
BHAT, B ;
HARRISON, DM .
TETRAHEDRON LETTERS, 1986, 27 (48) :5873-5874
[4]   CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - FORMATION OF A QUATERNARY CENTER AT C3A AND TOTAL SYNTHESIS OF THE MARINE ALKALOID (+)-ENT-DEBROMOFLUSTRAMINE-B [J].
BRUNCKO, M ;
CRICH, D ;
SAMY, R .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5543-5549
[5]   A new synthesis of (-)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-debromoflustramide B [J].
Cardoso, AS ;
Srinivasan, N ;
Lobo, AM ;
Prabhakar, S .
TETRAHEDRON LETTERS, 2001, 42 (38) :6663-6666
[6]   BROMO-SUBSTITUTED PHYSOSTIGMINE ALKALOIDS FROM A MARINE BRYOZOA FLUSTRA-FOLIACEA [J].
CARLE, JS ;
CHRISTOPHERSEN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) :4012-4013
[7]   MARINE ALKALOIDS .2. BROMO ALKALOIDS FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA - ISOLATION AND STRUCTURE ELUCIDATION [J].
CARLE, JS ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1586-1589
[8]   The first total synthesis of roquefortine D [J].
Chen, WC ;
Joullié, MM .
TETRAHEDRON LETTERS, 1998, 39 (46) :8401-8404
[9]   Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents [J].
Depew, KM ;
Marsden, SP ;
Zatorska, D ;
Zatorski, A ;
Bornmann, WG ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :11953-11963
[10]   Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C [J].
Fuchs, JR ;
Funk, RL .
ORGANIC LETTERS, 2005, 7 (04) :677-680