Journal of Organic Chemistry p. 1589 - 1598 (1990)
Update date:2022-09-26
Topics:
Paquette, Leo A.
Ross, Robert J.
Shi, Yao-Jun
Commercially available (+)-3-carene (4) is shown to be capable of efficient conversion to vinyl bromides 28, 46, and 49 and to vinyl stannane 44.All four compounds stem from (+)-3-norcaranone (23), an optically pure ketone best prepared by epoxidation of 4, followed by oxirane ring opening, acetylation, ozonolysis, and CrCl2-promoted reduction.The strong proclivity exhibited by 23 to enolize in the cyclopropyl carbinyl sense is used to advantage to gain entry to 28 and 44.Remarkably, the tosylhydrazone of (+)-3-norcaranone (45) is distinguished from its ketoneprogenitor 23 by its capacity for highly regioselective deprotonation from the alternative α-position.The crossover has made possible synthetic access to 46 and 49.Other chemistry of this class of compounds is also presented, inluding a route to 51, a vinyl bromide epimeric to 49.Especially relevant to future work in the ingenol area is the ability of these molecules to serve as nucleophiles.Several reactions involving 28 are provided as exemplary of this property.
View MoreContact:+86-0512-62857507
Address:Boji Science Park, No1688C,Taishan road, Suzhou ,China
Pengchen New Material Technology Co., Ltd.
Contact:+86-512-63680537
Address:99.6 km of national road 318, Meiyan Community,Pingwang Town, Wujiang District, Suzhou 215225
Shandong Jincheng Zhonghua Bio-pharmaceutical Co.,Ltd
Contact:+86-533-5415882
Address:Zichuan Economic Development Zone,Zibo City,Shandong Province,China
Wuhan Shangrisyn chemicals Technology Co.,Ltd(expird)
Contact:+86-027-84466317 __ +86-15387123698
Address:wuhan - china
Tianjin Ji Ping Jia Chemical Co., Ltd.
Contact:18622448868
Address:tianjin
Doi:10.1139/V10-061
(2010)Doi:10.1248/cpb.58.602
(2010)Doi:10.1039/c0nj00039f
(2010)Doi:10.1039/c2cc33885h
(2012)Doi:10.3987/COM-10-11970
(2010)Doi:10.1021/om201235c
(2012)