Journal of Organic Chemistry p. 7096 - 7099 (1993)
Update date:2022-08-03
Topics:
Kim
Choi
Cha
A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave tbe triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.
View MoreSPRING CHEMICAL INDUSTRY CO.,LTD
Contact:86-187-66672125
Address:linchi industry park.zouping
YanCheng LongShen Chemical Co.,Ltd.
Contact:+86-515-86668866
Address:No.13,Weiyi Road,Funing Aoyang Industrial Park
Yurui(Shanghai)Chemical Co.,Ltd
Contact:0086 21-50456736
Address:No.3188 Xiupu Road,Shanghai
Anhui Asahikasei Chemical Co., Ltd
Contact:86-551-4259770
Address:No. 88 Linquan Road Hefei Anhui China
Zipont chem(wuhan)Tech co.,Ltd
Contact:+86-27-87587198
Address:wuhan
Doi:10.1002/mrc.1260311105
(1993)Doi:10.1016/S0277-5387(00)83049-1
(1993)Doi:10.1016/0022-1139(93)02960-M
(1994)Doi:10.1039/a706985e
(1998)Doi:10.1016/j.tetlet.2016.02.106
(2016)Doi:10.1039/d0cc03150j
(2020)