Norrisolide: Total synthesis and related studies

被引：50
作者：
Brady, TP [1 ]
Kim, SH [1 ]
Wen, K [1 ]
Kim, C [1 ]
Theodorakis, EA [1 ]
机构：
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 24期
关键词：
natural products; oxidation; synthetic methods; terpenoids; total synthesis;
D O I：
10.1002/chem.200500513
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused gamma-lactone-gamma-lactol ring system attached to a bicyclic hydrophobic core. Our studies led to the development of a expedient synthesis of such gamma-lactone-gamma-lactol motifs based on ring expansion of a fused cyclopropyl ester. Highlights of the synthetic strategy toward norrisolide include the coupling of the two bicyclic systems by constructing a sterically demanding C9-C10 bond and the installation of the C19 oxygen at the last step of the synthesis via a Baeyer-Villiger oxidation.
引用
收藏
页码：7175 / 7190
页数：16
相关论文
共 123 条
[1]   Syntheses of oxygenated spongiane diterpenes from carvone.: Synthesis of dorisenone C [J].
Abad, A ;
Agulló, C ;
Cuñat, AC ;
García, AB .
TETRAHEDRON, 2005, 61 (08) :1961-1970
[2]   SPONGIAN PENTACYCLIC DITERPENES - STEREOSELECTIVE SYNTHESIS OF (-)-DENDRILLOL-1 [J].
ABAD, A ;
ARNO, M ;
CUNAT, AC ;
MARIN, ML ;
ZARAGOZA, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6861-6869
[3]  
Alper P. B., 1999, ANGEW CHEM, V111, P3379
[4]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[5]  
2-5
[6]   Synthesis and cytotoxic activity of novel C7-functionalized spongiane diterpenes [J].
Arnó, M ;
Betancur-Galvis, L ;
González, MA ;
Sierra, J ;
Zaragozá, RJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (14) :3171-3177
[7]   Synthesis of C-17-functionalized spongiane diterpenes:: Diastereoselective synthesis of (-)-spongian-16-oxo-17-al, (-)-acetyldendrillol-1, and (-)-aplyroseol-14 [J].
Arnó, M ;
González, MA ;
Zaragozá, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1242-1251
[8]   Diastereoselective synthesis of spongian diterpenes.: Total synthesis of the furanoditerpene (-)-spongia-13(16),14-diene. [J].
Arnó, M ;
González, MA ;
Zaragozá, RJ .
TETRAHEDRON, 1999, 55 (42) :12419-12428
[9]   Thermal rearrangements of vinylcyclopropanes to cyclopentenes [J].
Baldwin, JE .
CHEMICAL REVIEWS, 2003, 103 (04) :1197-1212
[10]   A NEW REACTION OF HYDRAZONES [J].
BARTON, DHR ;
OBRIEN, RE ;
STERNHELL, S .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :470-&
12345678910