2-BENZOPYRAN-3-ONES AS SYNTHETIC BUILDING-BLOCKS - REGIOSELECTIVE DIELS-ALDER ADDITIONS WITH SIMPLE OLEFINS LEADING TO AROMATIC STEROIDS

被引:18
作者
BLEASDALE, DA [1 ]
JONES, DW [1 ]
机构
[1] UNIV LEEDS,SCH MED,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 07期
关键词
MEDIATED TOTAL SYNTHESIS; STEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PRELIMINARY COMMUNICATION; ORTHO-QUINODIMETHANES; CONVENIENT REAGENT; PEPTIDE-SYNTHESIS; ORGANIC SYNTHESIS; CYCLOADDITION; SYSTEMS;
D O I
10.1039/p19910001683
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Benzopyran-3-one 1a undergoes strongly regioselective Diels-Alder additions to buta-1,3-diene, 2-methylpropene, but-1-ene and the olefin 9. The main adducts 17a and 17b from 1a and 1b respectively and the olefin 9(= 16) are derived by endo- and exo-addition to the re-face of 9(= 16). These adducts are converted into the 8-alpha,9-alpha-steroids 22a and 22b by a four-step sequence including Dieckmann cyclisation of 21a and 21b as the key step. The derived 8-alpha,9-alpha-steroids 24a and 24b can be epimerised at C-8 via the enones 26a and 26b and lithium-ammonia reduction. Other aromatic steroids obtained by this general route are the equilenin derivative 28 and the dihydronaphthalene 29.
引用
收藏
页码:1683 / 1692
页数:10
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