A novel, mild, and facile method to prepare 6-methylidene penem derivatives.
A novel and mild method was established to synthesize 6-methylidene penem compounds. This method entails a MgBr(2)/Et(3)N-promoted aldol-type condensation on 6-bromopenem 12 with an appropriately substituted aldehyde to yield the intermediate acetylated bromohydrin, which was smoothly converted to the final product with simultaneous deprotection of C3 carboxylic acid ester using activated zinc dust and phosphate buffer at pH 6.5. This process provides a useful variation of C-C bond formation method for penem derivatives and also serves as a practical synthetic method to prepare 6-exomethylenepenem derivatives without racemization at the C5 position.
Abe
Takao
T
Medical Research Laboratories, Wyeth Lederle Japan, Ltd., 1-6-34 Kashiwa-cho, Shiki-shi, Saitama 353-8511, Japan. takao_abe@meiji.co.jp
Sato
Chisato
C
Ushirogochi
Hideki
H
Sato
Koichi
K
Takasaki
Tsuyoshi
T
Isoda
Takeshi
T
Mihira
Ado
A
Yamamura
Itsuki
I
Hayashi
Kazuhiko
K
Kumagai
Toshio
T
Tamai
Satoshi
S
Shiro
Motoo
M
Venkatesan
Aranapakam M
AM
Mansour
Tarek S
TS
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D007769:Lactams