Extending pummerer reaction chemistry.: Synthesis of (±)-dibromophakellstatin by oxidative cyclization of an imidazole derivative

被引:63
作者
Feldman, KS [1 ]
Skoumbourdis, AP [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol0500113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The diastereoselective oxidative cyclization of a dihydrooroiclin derivative is reported. The thioimidate product formed by application of a new variant of the Pummerer reaction serves as a precursor to dibromophakellstatin.
引用
收藏
页码:929 / 931
页数:3
相关论文
共 54 条
[1]   Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by Pumerer-type reaction [J].
Akai, S ;
Kawashita, N ;
Satoh, H ;
Wada, Y ;
Kakiguchi, K ;
Kuriwaki, I ;
Kita, Y .
ORGANIC LETTERS, 2004, 6 (21) :3793-3796
[2]   Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings:: A convergent synthesis of diverse benzofuran neolignans [J].
Akai, S ;
Morita, N ;
Iio, K ;
Nakamura, Y ;
Kita, Y .
ORGANIC LETTERS, 2000, 2 (15) :2279-2282
[3]   New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks [J].
Braun, NA ;
Ousmer, M ;
Bray, JD ;
Bouchu, D ;
Peters, K ;
Peters, EM ;
Ciufolini, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4397-4408
[4]   Synthesis of axinohydantoins [J].
Carolina, A ;
Sosa, B ;
Yakushijin, K ;
Horne, DA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4498-4500
[5]   Hypervalent iodine-mediated vicinal syn diazidation:: Application to the total synthesis of (±)-dibromophakellstatin [J].
Chung, R ;
Yu, ES ;
Incarvito, CD ;
Austin, DJ .
ORGANIC LETTERS, 2004, 6 (22) :3881-3884
[6]   ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF 2-(PHENYLSULPHENYL) ALDEHYDES AND PRIMARY ALCOHOLS [J].
CRAIG, D ;
DANIELS, K ;
MACKENZIE, AR .
TETRAHEDRON LETTERS, 1991, 32 (47) :6973-6976
[7]   ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS AND ALPHA-HYDROXYKETONES [J].
CRAIG, D ;
DANIELS, K ;
MACKENZIE, AR .
TETRAHEDRON LETTERS, 1990, 31 (44) :6441-6444
[8]  
De Lucchi O., 1991, ORG REACTIONS, V40, P157, DOI DOI 10.1002/0471264180.0R040.03
[9]   Enantioselective strategy to the spirocyclic core of palau'amine and related bisguanidine marine alkaloids [J].
Dilley, AS ;
Romo, D .
ORGANIC LETTERS, 2001, 3 (10) :1535-1538
[10]   THE STRUCTURE OF DIBROMOISOPHAKELLIN FROM THE MARINE SPONGE ACANTHELLA-CARTERI [J].
FEDOREYEV, SA ;
UTKINA, NK ;
ILYIN, SG ;
RESHETNYAK, MV ;
MAXIMOV, OB .
TETRAHEDRON LETTERS, 1986, 27 (27) :3177-3180