Syntheses and absolute configurations of the marine sponge purines (+)-agelasimine-A and (+)-agelasimine-B

被引:27
作者
Ohba, M
Iizuka, K
Ishibashi, H
Fujii, T
机构
[1] Faculty of Pharmaceutical Sciences, Kanazawa University, Kanazawa 920, Takara-machi
关键词
D O I
10.1016/S0040-4020(97)10120-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total syntheses of (+)-agelasimine-A and (+)-agelasimine-B, adenine-related bicyclic diterpenoids isolated from the marine sponge Agelas mauritiana, have been achieved via a highly stereoselective route. On the basis of the present results, the absolute configurations of both alkaloids have been defined as shown in stereoformulas (+)-1a and (+)-1b, respectively. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:16977 / 16986
页数:10
相关论文
共 51 条
[11]   BIOLOGICALLY-ACTIVE METABOLITES FROM AGELAS-MAURITIANA [J].
FATHIAFSHAR, R ;
ALLEN, TM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (01) :45-50
[12]   SOME PHARMACOLOGICAL ACTIVITIES OF NOVEL ADENINE-RELATED COMPOUNDS ISOLATED FROM A MARINE SPONGE AGELAS-MAURITIANA [J].
FATHIAFSHAR, R ;
ALLEN, TM ;
KRUEGER, CA ;
COOK, DA ;
CLANACHAN, AS ;
VRIEND, R ;
BAER, HP ;
CASS, CE .
CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 1989, 67 (04) :276-281
[13]   LITHIUM AND POTASSIUM TRIALKYLBOROHYDRIDES - REAGENTS FOR DIRECT REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS TO SYNTHETICALLY VERSATILE ENOLATE ANIONS [J].
FORTUNATO, JM ;
GANEM, B .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2194-2200
[15]   MODEL EXPERIMENTS FOR ACETYLATION OF THE MARINE SPONGE PURINES AGELASIMINE-A AND AGELASIMINE-B [J].
FUJII, T ;
SAITO, T ;
CHIKAZAWA, J ;
OHBA, M ;
DATE, T .
HETEROCYCLES, 1994, 38 (04) :733-738
[16]  
FUJII T, 1994, CHEM PHARM BULL, V42, P2461
[17]   Conformational studies of some 1-hetera-2,6-diphenylcyclohexan-4-one oximes using NMR spectra-evidence for boat form contributions to trans-2,6-diphenyl systems [J].
Gurumani, V ;
Pandiarajan, K ;
Swaminathan, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (01) :29-35
[18]   ME3SICL/HMPA ACCELERATED CONJUGATE ADDITION OF CATALYTIC COPPER REAGENT - STEREOSELECTIVE SYNTHESIS OF ENOL SILYL ETHER OF ALDEHYDE [J].
HORIGUCHI, Y ;
MATSUZAWA, S ;
NAKAMURA, E ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1986, 27 (34) :4025-4028
[19]   PREPARATION OF (S)-(-)-4-METHYL-2-CYCLOHEXEN-1-ONE - A USEFUL CHIRAL BUILDING BLOCK [J].
HUA, DH ;
VENKATARAMAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1095-1097
[20]   ASYMMETRIC-SYNTHESIS OF CLERODANE DITERPENOIDS - TOTAL SYNTHESIS OF (-)-METHYL KOLAVENATE [J].
IIO, H ;
MONDEN, M ;
OKADA, K ;
TOKOROYAMA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) :358-359