Journal of Organic Chemistry p. 3592 - 3599 (1995)
Update date:2022-08-05
Topics:
Menez, Patrick Le
Fargeas, Valerie
Berque, Isabelle
Poisson, Jacques
Ardisson, Janick
et al.
A stereospecific synthesis of stannyl diene 5, corresponding to the C10-C15 fragment of (+/-)-tylosin aglycon 2, was reported.Silyl carbamate 16, submitted to the Hoppe homoaldolization conditions with propanal, gave the anti aldol product 17 in 89percent yield.Further treatment including oxidation of the silyl group led to lactone 21.The corresponding dihydrofuran 23 was then transformed into vinylstannane 25, via an efficient Kocienski rearrangement.An iodide exchange was performed on 25 and followed by a Stille coupling reaction with tributylstannyl acetylide.Stannyl cupration of the resulting silylated enyne 27 led in 44percent yield to a 1:1 mixture of the desired (E,E)-stannyl diene 5b and the unexpected (E,Z) isomer 29.The same reaction performed on desilylated enyne 28 delivered in 85percent yield the pure (E,E)-stannyl diene 5.
View MoreWuhan Fortuna Chemical Co.,Ltd
website:http://www.fortunachem.com
Contact:86-27-59207850
Address:Add: Room 2015, No.2 Building, Kaixin Mansion No.107 Jinqiao Avenue, Wuhan, China
YanCheng LongShen Chemical Co.,Ltd.
Contact:+86-515-86668866
Address:No.13,Weiyi Road,Funing Aoyang Industrial Park
Xi'an HO-SHINE Bio-Technology Co., Ltd
Contact:+86 (29) 8248-5435/18292020086
Address:No.6 Shiyuan Road Xian City Shaanxi Province, 710048 China
Contact:+86-25-83719363
Address:106-7 Chunnan Rd, Chunxi Town, Gaochun, Nanjing, China
Contact:0091-265-2313036
Address:311, ATLANTIS HEIGHTS SARABHAI MAIN ROAD,VADIWADI ,VADODARA
Doi:10.3762/bjoc.8.2
(2012)Doi:10.1021/ja01614a011
(1955)Doi:10.1016/S1734-1140(12)70878-2
(2012)Doi:10.1016/S0022-328X(00)98684-4
(1984)Doi:10.1246/cl.1984.131
(1984)Doi:10.1021/ol0606637
(2006)