Journal of Organic Chemistry p. 1611 - 1623 (1990)
Update date:2022-08-04
Topics:
Yamaguchi, Masahiko
Hasebe, Koichi
Higashi, Hirofumi
Uchida, Minoru
Irie, Akemi
Minami, Toru
The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part.The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxyanthracenes.The latters were air-oxidized to anthraquinones in the presence of K2CO3.The regiochemistry of the arene synthesis was studied.As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out.Pentacenequinones were synthesized from anthracenes, while anthraquinones gave naphthacenequinones.The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis.A formal synthesis of aklavinone was achieved.
View MoreContact:410-273-7300; 800-221-3953
Address:4609 Richlynn Dr., PO Box 369, Belcamp, MD, 21017-0369, USA
Hubei Xinjing New Material Co.,Ltd
Contact:+86-27-83313147
Address:Room402.#Bthe 7th,Headquarter of Huifeng Corporation Qiaokou District,Wuhan China
Shandong Bolode Bio-Technology Co., LTD
Contact:+86-0531-58966870
Address:136 Jingyi Road,Huaiyin District,Jinan,Shandong,China
Jiangsu Chiatai Qingjiang Pharmaceutical Co.,Ltd
Contact:+86-517-86283327
Address:9 North Hantai Road, Huaian, China
Penglai Qianwei Chemical Co., Ltd.
Contact:86-535-3357802
Address:Shahelu (north), Penglai, Shandong, China
Doi:10.1016/S0040-4020(01)88533-1
(1992)Doi:10.1016/S0957-4166(00)80274-8
(1992)Doi:10.1002/chem.201201892
(2012)Doi:10.1021/ml300396r
(2013)Doi:10.1021/om400016t
(2013)Doi:10.1021/jacs.7b04255
(2017)