The total synthesis of psymberin

被引:53
作者
Huang, Xianhai [1 ]
Shao, Ning [1 ]
Palani, Anandan [1 ]
Aslanian, Robert [1 ]
Buevich, Alexei [1 ]
机构
[1] Schering Plough Corp, Res Inst, Dept Chem Res, Kenilworth, NJ 07033 USA
关键词
D O I
10.1021/ol071068n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of a new member of the pederin family of natural products, psymberin 1, was accomplished. Using a recently reported novel and efficient PhI(OAc)(2) mediated oxidative entry to 2-(N-acylaminal)-substituted tetrahydropyrans as the key step, this total synthesis was executed in a convergent and efficient manner. The longest linear sequence of this synthesis was 22 steps starting from known 6.
引用
收藏
页码:2597 / 2600
页数:4
相关论文
共 19 条
[2]   Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family [J].
Cichewicz, RH ;
Valeriote, FA ;
Crews, P .
ORGANIC LETTERS, 2004, 6 (12) :1951-1954
[3]   The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride.: The merged stereochemical impact of α- and β-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles [J].
Evans, DA ;
Allison, BD ;
Yang, MG ;
Masse, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10840-10852
[4]   REDUCTION OF BETA-HYDROXY KETONES WITH CATECHOLBORANE - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF SYN 1,3-DIOLS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5190-5192
[5]   Stereochemical assignment of the C1-C6 fragment of psymberin by synthesis and natural product degradation [J].
Green, ME ;
Rech, JC ;
Floreancig, PE .
ORGANIC LETTERS, 2005, 7 (19) :4117-4120
[6]   BICYCLO[2.2.1]HEPTANES AS INTERMEDIATES IN THE SYNTHESIS OF STEROIDS - TOTAL SYNTHESIS OF ESTRONE [J].
GRIECO, PA ;
TAKIGAWA, T ;
SCHILLINGER, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2247-2251
[7]   Oxidative entry to α-oxy N-acyl aminals and hemiaminals:: efficient formation of 2-(N-acylaminal) substituted tetrahydropyrans [J].
Huang, Xianhai ;
Shao, Ning ;
Palani, Anandan ;
Aslanian, Robert .
TETRAHEDRON LETTERS, 2007, 48 (11) :1967-1971
[8]   Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].
Jiang, L ;
Job, GE ;
Klapars, A ;
Buchwald, SL .
ORGANIC LETTERS, 2003, 5 (20) :3667-3669
[9]   Synthesis and complete stereochemical assignment of psymberin/irciniastatin A [J].
Jiang, X ;
García-Fortanet, J ;
De Brabander, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11254-11255
[10]   Synthesis of psymberin analogues: Probing a functional correlation with the pederin/mycalamide family of natural products [J].
Jiang, Xin ;
Williams, Noelle ;
De Brabander, Jef K. .
ORGANIC LETTERS, 2007, 9 (02) :227-230