Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A

被引:51
作者
Jeong, Jeannie H. [1 ]
Weinreb, Steven M. [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol060556c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described is a convergent 13-step synthesis of a pentacyclic compound which has previously been transformed into haouamine A, therefore constituting a formal total synthesis of this unique marine alkaloid.
引用
收藏
页码:2309 / 2312
页数:4
相关论文
共 13 条
[1]   Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine [J].
Baldwin, SW ;
Debenham, JS .
ORGANIC LETTERS, 2000, 2 (02) :99-102
[2]   Total synthesis of (±)-haouamine A [J].
Baran, PS ;
Burns, NZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3908-3909
[3]   The first examples of ring-closing olefin metathesis of vinyl chlorides [J].
Chao, WC ;
Weinreb, SM .
ORGANIC LETTERS, 2003, 5 (14) :2505-2507
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]   Haouamines A and B:: A new class of alkaloids from the ascidian Aplidium haouarianum [J].
Garrido, L ;
Zubía, E ;
Ortega, MJ ;
Salvá, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :293-299
[6]  
Jones R. C. F., 2002, SYNTHETIC APPL 1 3 D
[7]   Synthesis of ortho-Methoxyphenylsulfonylsemicarbazides [J].
Lebegue, N ;
Bethegnies, G ;
Berthelot, P .
SYNTHETIC COMMUNICATIONS, 2004, 34 (06) :1041-1048
[8]  
NORDLANDER JE, 1978, TETRAHEDRON LETT, P4987
[9]  
PAYACK JF, 2002, ORG SYNTH, V79, P355
[10]   TITANIUM-MEDIATED CARBONYL OLEFINATIONS .1. METHYLENATIONS OF CARBONYL-COMPOUNDS WITH DIMETHYLTITANOCENE [J].
PETASIS, NA ;
BZOWEJ, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6392-6394