Concise Total Synthesis and Stereochemical Revision of all (-)-Trigonoliimines

被引:113
作者
Han, Sunkyu [1 ]
Movassaghi, Mohammad [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
STEREOCONTROLLED TOTAL-SYNTHESIS; ASYMMETRIC EPOXIDATION; ENANTIOSELECTIVE EPOXIDATION; OXIDATIVE REARRANGEMENT; ROOM-TEMPERATURE; ALKALOIDS; COMPLEXES; OLEFINS; BIOSYNTHESIS; DERIVATIVES;
D O I
10.1021/ja204597k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The concise and enantioselective total syntheses of (-)-trigonoliimines A, B, and C are described. Our unified strategy to all three natural products is based on asymmetric oxidation and reorganization of a single bistryptamine, a sequence of transformations with possible biogenetic relevance. We revise the absolute stereo chemistry of (-)-trigonoliimines A, B, and C.
引用
收藏
页码:10768 / 10771
页数:4
相关论文
共 45 条
[1]   Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].
Baran, PS ;
Richter, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396
[2]   A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].
Baran, PS ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905
[3]   Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes [J].
Boller, TM ;
Murphy, JM ;
Hapke, M ;
Ishiyama, T ;
Miyaura, N ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14263-14278
[4]   Stereocontrolled total synthesis of (+)-paraherquamide B [J].
Cushing, TD ;
SanzCervera, JF ;
Williams, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (03) :557-579
[5]   ENANTIOSELECTIVE SYNTHESIS OF TERTIARY ALPHA-HYDROXY CARBONYL-COMPOUNDS USING ((8,8-DICHLOROCAMPHORYL)SULFONYL)OXAZIRIDINE [J].
DAVIS, FA ;
WEISMILLER, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3715-3717
[6]   Adventures in sulfur-nitrogen [J].
Davis, Franklin A. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :8993-9003
[8]  
GAWLEY RE, 2009, CHEM SOC REV, V38, P3035
[9]  
Gueller R., 1993, HELV CHIM ACTA, V76, P1847
[10]  
HENTGES SG, 1980, J AM CHEM SOC, V102, P4263, DOI 10.1021/ja00532a050