Stereoselective synthesis of (-)-metasequoic acid B

被引:18
作者
Abad, A
Agullo, C
Arno, M
Cantin, A
Cunat, AC
Meseguer, B
Zaragoza, RJ
机构
[1] Departamento de Química Orgánica, Facultad de Químicas, Universidad de Valencia, 46100-Burjassot, Valencia
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 12期
关键词
D O I
10.1039/a700354d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of the ent-labdane diterpene(-)-metasequoic acid B (ent-2) and its corresponding methyl ester (ent-3) starting from (R)-(-)-carvone 6 is described. The synthesis is based on the construction of a phenanthrenone system 5 which is converted into the ent-labdane skeleton after selective cleavage of the C(13)-C(14) bond.
引用
收藏
页码:1837 / 1843
页数:7
相关论文
共 24 条
[21]  
SMITH MB, 1994, ORG SYNTH, P673
[22]   CONSTITUENTS OF MARINE PLANTS .77. THE STRUCTURES OF CYTOTOXIC DITERPENES CONTAINING BROMINE FROM THE MARINE RED ALGA LAURENCIA-OBTUSA (HUDSON) LAMOUROUX [J].
TAKEDA, S ;
KUROSAWA, E ;
KOMIYAMA, K ;
SUZUKI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (11) :3066-3072
[23]   A GENERAL-METHOD FOR THE SELECTIVE REDUCTION OF KETONES IN THE PRESENCE OF ENONES [J].
WARD, DE ;
RHEE, CK ;
ZOGHAIB, WM .
TETRAHEDRON LETTERS, 1988, 29 (05) :517-520
[24]   DITERPENE RESIN ACIDS FROM THE NEEDLE OLEORESIN OF PINUS-STROBUS [J].
ZINKEL, DF ;
MAGEE, TV .
PHYTOCHEMISTRY, 1987, 26 (03) :769-774