Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: A practical and versatile synthesis of psilocin

被引:50
作者
Gathergood, N
Scammells, PJ
机构
[1] Monash Univ, Victorian Coll Pharm, Dept Med Chem, Parkville, Vic 3052, Australia
[2] Deakin Univ, Sch Biol & Chem Sci, Geelong, Vic 3217, Australia
关键词
D O I
10.1021/ol0341039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 4-hydroxytryptamine scaffold of psilocin was successfully prepared via palladium-catalyzed cyclization of protected N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline and an appropriately substituted silyl acetylene. Removal of the protecting groups afforded psilocin in good yield.
引用
收藏
页码:921 / 923
页数:3
相关论文
共 27 条
[1]  
BRIMBLECOMBE RW, 1975, HALLUCINOGENIC AGENT, P106
[2]  
Brown R.T., 1979, COMPREHENSIVE ORGANI, V4, P411
[3]   THE CHEMISTRY OF THE PSYCHOTOMIMETIC SUBSTANCES [J].
DOWNING, DF .
QUARTERLY REVIEWS, 1962, 16 (02) :133-162
[4]   PSILOCYBIN UND PSILOCIN, ZWEI PSYCHOTROPE WIRKSTOFFE AUS MEXIKANISCHEN RAUSCHPILZEN [J].
HOFMANN, A ;
HEIM, R ;
BRACK, A ;
KOBEL, H ;
FREY, A ;
OTT, H ;
PETRZILKA, T ;
TROXLER, F .
HELVETICA CHIMICA ACTA, 1959, 42 (05) :1557-+
[5]  
HOFMANN A, 1971, B NARCOTICS, V23, P3
[6]   PSILOCYBIN, EIN PSYCHOTROPER WIRKSTOFF AUS DEM MEXIKANISCHEN RAUSCHPILZ PSILOCYBE-MEXICANA HEIM [J].
HOFMANN, A ;
HEIM, R ;
BRACK, A ;
KOBEL, H .
EXPERIENTIA, 1958, 14 (03) :107-109
[7]   General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety [J].
Kondo, Y ;
Kojima, S ;
Sakamoto, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6507-6511
[8]   PALLADIUM-CATALYZED COUPLING OF 2-BROMOANILINES WITH VINYLSTANNANES - A REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED INDOLES [J].
KROLSKI, ME ;
RENALDO, AF ;
RUDISILL, DE ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1170-1176
[9]  
KUTNEY JP, 1977, TOTAL SYNTHESIS NATU, V3, P273
[10]   SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED HETEROANNULATION OF INTERNAL ALKYNES [J].
LAROCK, RC ;
YUM, EK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6689-6690