Synthesis and reactions of flav-3-en-3-ols

被引:7
作者
Coetzee, J
Malan, E
Ferreira, D [1 ]
机构
[1] Univ Mississippi, Sch Pharm, Pharmaceut Sci Res Inst, Natl Ctr Nat Prod Res, University, MS 38677 USA
[2] Univ Orange Free State, Dept Chem, ZA-9300 Bloemfontein, South Africa
基金
美国农业部;
关键词
flavanoids; flav-3-en-3-ols; regioselection; stereoselection; alpha-sulfenylation;
D O I
10.1016/S0040-4020(00)00102-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Flavan-3,4-diols are subject to facile conversion into flav-3-en-3-ols which are versatile precursors in flavonoid synthesis. The flavan-3-ones undergo a unique Lewis acid assisted alpha-sulfenylation reaction with benzyl mercaptan in the presence of SnCl4. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1819 / 1824
页数:6
相关论文
共 30 条
[21]  
PORTER LJ, 1986, J CHEM RES-S, P86
[22]   ALPHA-HYDROXYCHALCONES AS INTERMEDIATES IN FLAVONOID BIOGENESIS - SIGNIFICANCE OF RECENT CHEMICAL ANALOGIES [J].
ROUX, DG ;
FERREIRA, D .
PHYTOCHEMISTRY, 1974, 13 (10) :2039-2048
[23]   HISTOCHEMICAL ASSAY OF PROANTHOCYANIDIN HETEROGENEITY IN CELL-CULTURES [J].
STAFFORD, HA ;
LESTER, HH ;
WEIDER, RM .
PLANT SCIENCE, 1987, 52 (1-2) :99-104
[25]   ENZYMIC REGULATION OF PROCYANIDIN BIOSYNTHESIS - LACK OF A FLAV-3-EN-3-OL INTERMEDIATE [J].
STAFFORD, HA .
PHYTOCHEMISTRY, 1983, 22 (12) :2643-2646
[26]   PROANTHOCYANIDINS AND POTENTIAL PRECURSORS IN NEEDLES OF DOUGLAS-FIR AND IN CELL-SUSPENSION CULTURES DERIVED FROM SEEDLING SHOOT TISSUES [J].
STAFFORD, HA ;
LESTER, HH .
PLANT PHYSIOLOGY, 1981, 68 (05) :1035-1040
[27]  
VANRENSBURG H, 1999, CHEM RES S, V45, P450
[28]  
Yoshida Y, 1999, HETEROCYCLES, V50, P681
[29]   ASYMMETRIC SULFENYLATION OF TIN(II) ENOLATES OF KETONES AND 3-ACYL-2-OXAZOLIDONES - APPLICATION TO THE SYNTHESIS OF OPTICALLY-ACTIVE EPOXIDES [J].
YURA, T ;
IWASAWA, N ;
CLARK, R ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1986, (11) :1809-1812
[30]   SYNTHESIS OF A FLAV-3-EN-3-OL VIA CINNAMYLPHENOL [J].
ZANAROTTI, A .
TETRAHEDRON LETTERS, 1982, 23 (38) :3963-3964