- Total Synthesis of (+/-)-Perezone
-
A total synthesis of (+/-)-perezone (1) proceeding in 18percent overall yield is described.The sequence starts from 5-bromopiperonal (2) and proceeds by way of 7, making use of an AgO-assisted oxidative dealkylation step to unmask the hydroxy-p-quinone-type system characteristic of 1.
- Sanchez, Ignacio H.,Mendoza, Serafin,Calderon, Mireya,Larraza, Maria Isabel,Flores, Humberto J.
-
-
Read Online
- Total Synthesis of (?)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone
-
The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (?)-perezoperezone from commercially available 3,5-dimethoxytoluene.
- Long, Yang,Ding, Yiming,Wu, Hai,Qu, Chunlei,Liang, Hong,Zhang, Min,Zhao, Xiaoli,Long, Xianwen,Wang, Shu,Puno, Pema-Tenzin,Deng, Jun
-
supporting information
p. 17552 - 17557
(2019/11/16)
-
- Synthesis of Hydroxyquinones and Related Compounds: Semisquaric Acids, (+/-)-Terreic Acid, (+/-)-Perezone, and (+/-)-Isoperezone
-
tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.
- Enhsen, Alfons,Karabelas, Kostas,Heerding, Julia M.,Moore, Harold W.
-
p. 1177 - 1185
(2007/10/02)
-