The first enantioselective total synthesis of (-)-arisugacin A

被引:23
作者
Cole, KP [1 ]
Hsung, RP [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(02)02094-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantioselective synthesis of (-)-arisugacin A in 17 steps is described here, featuring a CBS asymmetric ketone reduction and a highly stereoselective formal [3+3] cycloaddition approach. This concise synthesis of the enantiomer unambiguously confirms the original assignment of the absolute configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8791 / 8793
页数:3
相关论文
共 45 条
[1]   THE REDUCTIVE CONVERSION OF SOME CYCLIC AND ACYCLIC VIC-EPOXIDES TO ALCOHOLS BY MEANS OF LITHIUM ALUMINUM-HYDRIDE ALUMINUM TRICHLORIDE [J].
ANDREJEVIC, V ;
BJELAKOVIC, M ;
MIHAILOVIC, MM ;
MIHAILOVIC, ML .
HELVETICA CHIMICA ACTA, 1985, 68 (07) :2030-2032
[2]   Total synthesis of forskolin studies .3. Studies related to an asymmetric synthesis [J].
Calvo, D ;
Port, M ;
Delpech, B ;
Lett, R .
TETRAHEDRON LETTERS, 1996, 37 (07) :1023-1024
[3]   The total synthesis of (±)-arisugacin A [J].
Cole, KP ;
Hsung, RP ;
Yang, XF .
TETRAHEDRON LETTERS, 2002, 43 (18) :3341-3345
[4]   A SHORT AND EFFICIENT ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE FOR THE TOTAL SYNTHESIS OF FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD .
TETRAHEDRON LETTERS, 1989, 30 (52) :7297-7300
[5]   A NEW PROCESS FOR THE GENERATION OF 1,3,2-OXAZABOROLIDINES, CATALYSTS FOR ENANTIOSELECTIVE SYNTHESIS [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1992, 33 (29) :4141-4144
[6]   ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE IN THE TOTAL SYNTHESIS OF FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD ;
MOHRI, T .
TETRAHEDRON LETTERS, 1988, 29 (49) :6409-6412
[7]   AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].
COREY, EJ ;
SHIBATA, S ;
BAKSHI, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863
[8]   A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
BAKSHI, RK .
TETRAHEDRON LETTERS, 1990, 31 (05) :611-614
[9]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[10]   A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S ;
CHEN, CP ;
SINGH, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926