Journal of the American Chemical Society p. 669 - 673 (1989)
Update date:2022-08-02
Topics:
Hamada
Kondo
Shibata
Shioiri
Didemnins A and B (1 and 2), cytotoxic cyclic peptides from a Caribbean tunicate Trididemnum solidum, have been efficiently prepared by a convergent scheme from two key eastern and western fragments. Efficient routes to derivatives of the constituents of didemnis were explored. Benzyl (2RS,4S)-[O-(tert-butyldimethylsilyl)hydroxyisovaleryl]propionate (Hip derivative) was prepared from 2-hydroxyisovaleric acid by use of C-acylation of Meldrum's acid with diethyl phosphorocyanidate as a key step. Derivatives of (3S,4R,5S)-isostatine (Ist) were prepared from Boc-(R)-alloisoleucine. Methylation of Boc-(R)-Leu-OH and Z-(S)-Tyr-OH respectively afforded the corresponding N-methyl and N,O-dimethyl derivatives. The key eastern fragment, (2RS,4S)-Hip-(S)-Leu-(S)-Pro-OBzl (3), was prepared stepwise from (S)-Pro-OBzl, while Boc-(R)-MeLeu-(S)-Thr[Z-(S)-MeTyr(Me)]-(3S,4R,5S)-Ist(TBDMS)-OH (4), the key western fragment for didemnin A (1), was prepared from Ist derivatives. Coupling of 3 with 4 and cyclization, followed by deprotection, afforded didemnin A (1), which was converted to didemnin B (2).
View MoreTaizhou Elitechemie MediPharma Technology Co.,Ltd.
Contact:+86-523-86810021
Address:Building G14,NO.1 Avenue,China Medical City, Taizhou, Jiangsu,China
Tianjin Puck Rice Chemicals Co., Ltd.
Contact:022-58054572
Address:Weidi Road
Laizhou City Laiyu Chemical CO.,Ltd
Contact:+86-535-2719337/2719339
Address:Chenggang road zhuyou laizhou City Shangdong China
Weifang Dongxing Chitosan Factory
website:http://dxchitosan.lookchem.com/
Contact:13475651157
Address:Weifang city ,shandong province
website:http://www.joyochem.com
Contact:0531-82687558, 0531-82687326
Address:Factory Building 11, Jinan Comprehensive free trade zone, Shandong, China
Doi:10.1016/j.ejmech.2018.01.045
(2018)Doi:10.1039/c1cc11256b
(2011)Doi:10.1021/jo01283a011
(1967)Doi:10.1021/jo00003a055
(1991)Doi:10.1021/bi00603a020
(1978)Doi:10.1016/j.crci.2010.12.001
(2011)