Tetrahedron p. 63 - 70 (1982)
Update date:2022-08-04
Topics:
Bertz, Steven H.
Rihs, G.
Woodward, R.B.
A simple and efficient two-step preparation of bicyclo<3.3.0>octane-3,7-dione starting from the sodium enolate of dimethyl 3-ketoglutarate and glyoxal is described.This is an unprecedented case in which a condensation reaction of glyoxal is more successful under vigorous conditions (refluxing methanol) than under much milder ones (buffered water at ambient temperature).The major product (after hydrolysis-decarboxylation) from the analogous sequence with phenylglyoxal is 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone, the result of a Dieckmann reaction in addition to the Michael and aldol reactions.Only the latter two occur in aqueous buffers, where the product after hydrolysis-decarboxylation is 1-phenylbicyclo<3.3.0>octane-3,7-dione.The X-ray crystal structure of the indanone reveals a novel hydrogen bonding phenomenon.
View MoreTianjin Crest Pharmaceutical R&D Co., Ltd. (Tianjin Yao Technology Development Co., Ltd.)
Contact:+86-22-66211386
Address:Building B5-405, No, 80 4th Avenue, TEDA, Tianjin, China P.R. 300457
Qingdao Pana-Life Biochem Co.,Ltd.
Contact:86-532-87683902
Address:No.967 Dalao Road, Licang Zone, Qingdao City,Shandong, China 266021
Chemvon Biotechnology Co. Ltd.
website:http://www.chemvon.com
Contact:86-21-58550039;86-21-31268550-8004
Address:Suite B-10#, 6999 Chuansha Road, Pudong District, Shanghai 201202, China
Hunan Dinuo Pharmaceutical Co.,Ltd.
Contact:86-731-88280100*8561
Address:Bio-pharmaceutical industrial park, Liuyang, Hunan, China
Nantong Kaixin Pharma Chemical Co.,Ltd.
Contact:86-513-85250786
Address:2-1103 Huachen Mansion, 111 Gongnong Road,Nantong, Jiangsu, China
Doi:10.1002/ardp.19823150704
(1982)Doi:10.1021/jo00147a010
(1982)Doi:10.1021/jo00144a014
(1982)Doi:10.1021/jo00145a017
(1982)Doi:10.1039/DT9820000999
(1982)Doi:10.1016/S0040-4039(00)87083-5
(1982)