Cascade radical cyclisations leading to polycyclic diterpenes.: Total synthesis of (±)-spongian-16-one

被引:45
作者
Pattenden, G [1 ]
Roberts, L [1 ]
Blake, AJ [1 ]
机构
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 05期
关键词
D O I
10.1039/a708042e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cascade of three consecutive 6-endo-trig radical cyclisations from the polyene acyl radical intermediate 12 derived from the selenoate 11 is used to construct the trans,anti,trans,anti,cis-tetracyclic keto lactone 20 in one step. Manipulation of the ketone function in 20 to the corresponding gem-dimethyl substituted carbon then completed a concise synthesis of the marine metabolite spongian-16-one 1.
引用
收藏
页码:863 / 868
页数:6
相关论文
共 33 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, TETRAHEDRON LETT, P3013
[3]   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
[4]   NEW DITERPENES FROM SPONGIA-OFFICINALIS [J].
CIMINO, G ;
MORRONE, R ;
SODANO, G .
TETRAHEDRON LETTERS, 1982, 23 (40) :4139-4142
[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]  
DOUBLE PJ, UNPUB
[7]  
GODLESKI SA, 1983, J ORG CHEM, V48, P2101, DOI 10.1021/jo00160a035
[8]   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
[9]   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
[10]   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