Total synthesis and stereochemistry of (-)-cacospongionolide F

被引:26
作者
Demeke, D [1 ]
Forsyth, CJ [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol027438j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] The most recently described member of the cacospongionolide class of marine natural products has been assembled using a diastereochernically divergent total synthesis strategy that independently establishes the complete stereochemistry of cacospongionolide F and provides a new entry toward expansion of this phospholipase A(2) inhibitor chemotype.
引用
收藏
页码:991 / 994
页数:4
相关论文
共 25 条
[1]   Total syntheses of (+)- and (-)-cacospongionolide B:: New insight into structural requirements for phospholipase A2 inhibition [J].
Cheung, AK ;
Snapper, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11584-11585
[2]   A three-step and enantioselective synthesis of (-)-(S)- or (+)-(R)-2-(furan-3-yl)-3,6-dihydro-2H-pyrans [J].
de Rosa, M ;
Solladié-Cavallo, A ;
Scettri, A .
TETRAHEDRON LETTERS, 2000, 41 (10) :1593-1596
[3]   Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues [J].
De Rosa, M ;
Giordano, S ;
Scettri, A ;
Sodano, G ;
Soriente, A ;
Pastor, PG ;
Alcaraz, MJ ;
Payá, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (17) :3232-3238
[4]   A new cacospongionolide derivative from the sponge Fasciospongia cavernosa [J].
De Rosa, S ;
Crispino, A ;
De Giulio, A ;
Iodice, C ;
Amodeo, P ;
Tancredi, T .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1316-1318
[5]   A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides [J].
De Rosa, S ;
Crispino, A ;
De Giulio, A ;
Iodice, C ;
Benrezzouk, R ;
Terencio, MC ;
Ferrándiz, L ;
Alcaraz, MJ ;
Payá, M .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (07) :931-935
[6]   Total synthesis of (-+)-dysidiolide [J].
Demeke, D ;
Forsyth, CJ .
TETRAHEDRON, 2002, 58 (32) :6531-6544
[7]   Novel total synthesis of the anticancer natural product dysidiolide [J].
Demeke, D ;
Forsyth, CJ .
ORGANIC LETTERS, 2000, 2 (20) :3177-3179
[8]   Further bioactive sesterterpenes from the tyrrhenian sponge Fasciospongia cavernosa [J].
DeRosa, S ;
DeGiulio, A ;
Crispino, A ;
Iodice, C ;
Tommonaro, G .
NATURAL PRODUCT LETTERS, 1997, 10 (04) :267-274
[9]   CACOSPONGIONOLIDE - A NEW ANTITUMORAL SESTERTERPENE, FROM THE MARINE SPONGE CACOSPONGIA-MOLLIOR [J].
DEROSA, S ;
DESTEFANO, S .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5020-5023
[10]   25-DEOXYCACOSPONGIONOLIDE-B AND CACOSPONGIONOLIDE-C, 2 NEW TERPENOIDS FROM THE SPONGE FASCIOSPONGIA-CAVERNOSA [J].
DEROSA, S ;
PULITI, R ;
CRISPINO, A ;
DEGIULIO, A ;
DESENA, C ;
IODICE, C ;
MATTIA, CA .
TETRAHEDRON, 1995, 51 (39) :10731-10736