Tetrahedron p. 13087 - 13104 (1998)
Update date:2022-08-04
Topics:
Maezaki, Naoyoshi
Matsumori, Yuki
Shogaki, Takeshi
Soejima, Motohiro
Ohishi, Hirofumi
Tanaka, Tetsuaki
Iwata, Chuzo
A new mode of synthesizing chiral 2,2,5-trisubstituted tetrahydropyran is described, in which two chiral centers are simultaneously introduced via facial and group selective nucleophilic acetal cleavage reaction of a bicyclic acetal 1, thereby accomplishing 1,3- and 1,6-asymmetric induction. It is revealed that acetal cleavage of the pro-R C-O bond and nucleophilic attack opposite the cleaved bond proceed preferentially. With TiCl4 and allyltrimetylsilane at -100 °C, the selectivity of acetal fission is 10:1 and that of nucleophilic attack is 12:1. This reaction is successfully applied to a total synthesis of marine antibiotics, (-)-malyngolide.
View MoreShaanxi HuaTai Bio-fine chemical company Ltd
Contact:86-029-87862197
Address:No. 5, 3rd Floor, 29 Yanta North Road, Beilin Dist.
Shijiazhuang Frontierchem Co., Ltd.
Contact:+86-311-89271196
Address:4-4-202 No.15 Biandian Street,Shijiazhuang
Shenyang Mole pharmaceutical Technology Development Co.,Ltd
Contact:+86-24-31204918/13889278616
Address:No.44, wanliutang road, shenhe District of Shenyang
jintan yufan Medicine Raw materials Co.,Ltd.
Contact:86-519-82808282
Address:6th,Jincheng Huangzhuang
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Doi:10.1016/S0957-4166(98)00330-9
(1998)Doi:10.1139/v69-046
(1969)Doi:10.1016/S0040-4020(00)01092-9
(2001)Doi:10.1002/adsc.201500801
(2016)Doi:10.1039/j19690000153
(1969)Doi:10.1271/bbb.62.1875
(1998)