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 MoreContact:+86-571-28186845
Address:Room 1224,Eastcom Mansion,398 Wensan Road,Hangzhou,310013 China
website:http://www.maisonchem.com.cn
Contact:0086-311-83833777
Address:Leitou industrial district, xinji, shijiazhuang city, hebei province,
SHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Contact:+86-10-67147360/67107388
Address:No.18 Guangming Zhongjie, Chongwen District, Beijing, 100061, China
website:https://www.sinoshiny.com/products
Contact:+86-20-62802632;62802633
Address:Room 330 GIGCAS Building,No.511 Kehua Street,Tianhe District
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)
