Cascade radical processes leading to polycycle constructions. The total synthesis of spongian-16-one

被引:27
作者
Pattenden, G
Roberts, L
机构
[1] Department of Chemistry, Nottingham University
关键词
D O I
10.1016/0040-4039(96)00740-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise total synthesis of the marine sponge metabolite spongian-16-one 1, which features a novel cascade of three consecutive 6-endo-trig radical cyclisations from a polyene acyl radical intermediate as a key step, viz 9 --> 10, is described. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:4191 / 4194
页数:4
相关论文
共 25 条
[1]   Acyl radical-mediated polyene cyclisations directed towards steroid ring synthesis [J].
Batsanov, A ;
Chen, LG ;
Gill, GB ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (01) :45-55
[2]  
CAHIEZ G, 1978, ATETRAHEDRON LETT, P3013
[3]   10 NEW REARRANGED SPONGIAN DITERPENES FROM 2 DYSIDEA SPECIES [J].
CARMELY, S ;
COJOCARU, M ;
LOYA, Y ;
KASHMAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4801-4807
[4]   Consecutive-6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions [J].
Chen, LG ;
Gill, GB ;
Pattenden, G ;
Simonian, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (01) :31-43
[5]   STEREOSELECTIVE SYNTHESIS OF THE ENANTIOMER OF THE NOVEL MARINE DITERPENE ISOAGATHOLACTONE, ENT-13(16),14-SPONGIADIEN-12-ALPHA-OL, AND THE PARENT HYDROCARBON ISOCOPALANE FROM METHYL ISOCOPALATE [J].
DEMIRANDA, DS ;
BRENDOLAN, G ;
IMAMURA, PM ;
SIERRA, MG ;
MARSAIOLI, AJ ;
RUVEDA, EA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4851-4858
[6]  
GODLESKI SA, 1983, J ORG CHEM, V48, P2101, DOI 10.1021/jo00160a035
[7]   MARINE NATURAL-PRODUCTS FROM THE ATLANTIC ZONE .42. NEW ANTIMICROBIAL DITERPENES FROM THE SPONGE SPONGIA-OFFICINALIS [J].
GONZALEZ, AG ;
ESTRADA, DM ;
MARTIN, JD ;
MARTIN, VS ;
PEREZ, C ;
PEREZ, R .
TETRAHEDRON, 1984, 40 (20) :4109-4113
[8]   THE CONSTITUENTS OF MARINE SPONGES .5. THE ISOLATION FROM CHELONAPLYSILLA-VIOLACEA (DENDROCERATIDA) OF APLYVIOLENE AND OTHER DITERPENES, AND THE DETERMINATION OF THE CRYSTAL-STRUCTURE OF APLYVIOLENE [J].
HAMBLEY, TW ;
POINER, A ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1861-1870
[9]   ENANTIOSELECTIVE SYNTHESIS OF A C/D-RING SYNTHON FOR THE PREPARATION OF VITAMIN-D3 METABOLITES [J].
HATAKEYAMA, S ;
NUMATA, H ;
OSANAI, K ;
TAKANO, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) :1893-1895
[10]   STEREOSELECTIVE SYNTHESIS OF THE NOVEL MARINE DITERPENE (+)-ISOAGATHOLACTONE [J].
IMAMURA, PM ;
SIERRA, MG ;
RUVEDA, EA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (15) :734-735