TOTAL SYNTHESES OF THE DITERPENOIDS (-)-KOLAVENOL AND (-)-AGELASINE-B

被引:51
作者
PIERS, E
ROBERGE, JY
机构
[1] Department of Chemistry, University of British Columbia, Vancouver, BC V6T 1Z1
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4039(00)60896-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trans-clerodane diterpenoids (-)-kolavenol (2) and (-)-agelasine B (1) have been prepared from the enantiomerically pure decalone 3. The key steps of the syntheses involve the stereoselective alkylation of the nitrile 4 (to give 5), the efficient coupling of the iodides 10 and 11 to produce the clerodane skeleton 12, and the electrochemical reduction of 16 to provide (-)-1.
引用
收藏
页码:6923 / 6926
页数:4
相关论文
共 14 条
[1]   REAGENTS AND SYNTHETIC METHODS .61. REACTION OF HINDERED TRIALKYSILYL ESTERS AND TRIALKYLSILYL ETHERS WITH TRIPHENYLPHOSPHINE DIBROMIDE - PREPARATION OF CARBOXYLIC-ACID BROMIDES AND ALKYL BROMIDES UNDER MILD NEUTRAL CONDITIONS [J].
AIZPURUA, JM ;
COSSIO, FP ;
PALOMO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4941-4943
[2]   CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].
BAILEY, WF ;
PUNZALAN, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406
[3]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[4]   A GENERAL-SYNTHESIS OF 7,9-DIALKYLADENINIUM SALTS [J].
FUJII, T ;
SAITO, T ;
SAKUMA, T ;
MINAMI, M ;
INOUE, I .
HETEROCYCLES, 1981, 16 (02) :215-220
[5]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :978-980
[6]   DIMETHYLBORON BROMIDE AND DIPHENYLBORON BROMIDE - CLEAVAGE OF ACETALS AND KETALS [J].
GUINDON, Y ;
YOAKIM, C ;
MORTON, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3912-3920
[7]  
LIO H, 1987, J CHEM SOC CHEM COMM, P358
[8]  
LIO H, 1985, J CHEM SOC CHEM COMM, P774
[9]   HIGHER-ISOPRENOIDS .10. DITERPENOIDS FROM THE OLEORESIN OF HARDWICKIA-PINNATA .3. KOLAVENOL, KOLAVELOOL AND A NOR DITERPENE HYDROCARBON [J].
MISRA, R ;
PANDEY, RC ;
DEV, S .
TETRAHEDRON, 1979, 35 (08) :985-987
[10]   AGELASINE-A, AGELASINE-B, AGELASINE-C AND AGELASINE-D, NOVEL BICYCLIC DITERPENOIDS WITH A 9-METHYLADENINIUM UNIT POSSESSING INHIBITORY EFFECTS ON NA,K-ATPASE FROM THE OKINAWAN SEA SPONGE AGELAS SP 1) [J].
NAKAMURA, H ;
WU, HM ;
OHIZUMI, Y ;
HIRATA, Y .
TETRAHEDRON LETTERS, 1984, 25 (28) :2989-2992