TY - JOUR
T1 - An improved synthetic method for dL-griseofulvin and its 2-S-analogue
AU - Yamato, Masatoshi
AU - Takeuchi, Yasuo
AU - Tomozane, Hideo
N1 - Publisher Copyright:
© 1990 Georg Thieme Verlag. All rights reserved.
PY - 1990
Y1 - 1990
N2 - An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.
AB - An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.
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U2 - 10.1055/s-1990-26942
DO - 10.1055/s-1990-26942
M3 - Article
AN - SCOPUS:0025078711
VL - 1990
SP - 569
EP - 570
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 7
ER -