Journal of Organic Chemistry p. 608 - 614 (1984)
Update date:2022-08-02
Topics:
Knapp, Spencer
Trope, Adrea F.
Theodore, Michael S.
Hirata, Naonori
Barchi, Joseph J.
A practical two-step procedure for the title transformation has been developed.Treatment of cyclic ketones with (CH3S)3CLi gave adducts 6 and 13-17, which underwent ring expansion at 75 deg C in the presence of CuBF4*4CH3CN to the keto thioketals 7 and 18-21.In the cases examined the reaction was highly regioselective, giving the product resulting from migration of the more substituted carbon.The procedure has been used to prepare a key bicyclic intermediate (33) for a total synthesis of (+/-)-coriolin (1).An alternative synthesis of 33 suggests that were there is steric crowding in the vicinity of the tris(methylthio)methyl group of the adduct, the bond migration is controlled by the location of the obtruding group.
View MoreTIANJIN DONGRUXIANG MINERALS MARKETING CO.,LTD(expird)
Contact:22-58516360
Address:tianjin
Luojiang Chenming Biological Products Co
Contact:+86 15000297032
Address:GROUP NO.4, HE SHENG VILLAGE, PANLONG TOWN,
WEIFANG RICHEM INTERNATIONAL LTD
Contact:86-536-2222176
Address:weifang,shandong
Shanghai Balmxy Pharmaceutical Co., Ltd
Contact:0086-21-24206007
Address:Room 402, 15#, No. 909 wangyue Road, shanghai, P. R. China
Jiangxi Province Bethel Pharmaceutical Co., Ltd.
Contact:+86-795-259 3456 ，+86-15957688008 13566650571
Address:Huangjindui Chemical Park， Shanggao County ，Yichun city，Jiangxi Province
Doi:10.1016/j.tetlet.2006.01.158
(2006)Doi:10.1016/j.jorganchem.2020.121214
(2020)Doi:10.1021/jm00335a016
(1964)Doi:10.1016/0031-9422(81)84053-8
(1981)Doi:10.1016/S0040-4039(00)81548-8
(1983)Doi:10.1021/ja0585477
(2006)
