Journal of the Chemical Society. Perkin transactions I p. 135 - 139 (1983)
Update date:2022-08-05
Topics:
Nakano, Tatsuhiko
Hernandez, Maria Isabel
The highly efficient, stereoselective syntheses of (+/-)-isoagatholactone (1a) and (+/-)-12α-hydroxyspongia-13(16),14-diene (3e), a fundamental skeleton of spongiadiol (3a) and its related furanoid diterpenes, are described. (+/-)-Labda-8(20),13-dien-15-oic acid (6), chosen as the starting material, was cyclised to the known tricyclic compound (2b), which after methylation was subjected to photooxygenation, yielding the allylic alcohol (7a).Refluxing of the alcohol (7a) with 3.5percent sulphuric acid in dioxan afforded the lactone (1b), which after reduction with lithium aluminium hydride led to the diol (2g).Subsequent oxidation of this diol with Collins reagent provided the desired compound (1a).The key precursor for the synthesis of compound (3e) was the allylic alcohol (7a) obtained above.On epoxidation the alcohol (7a) gave the epoxide (13), which by the action with lithium di-isopropylamide led to the α,β-unsaturated γ-lactone (14).Subsequent reduction of this lactone with di-isobutylaluminium hydride afforded the furan (3e).
View MoreHuzhou City Linghu Xinwang Chemical Co.,Ltd.
Contact:86-572-3948695/3945236
Address:huzhou
Contact:86-15588110016
Address:LINYI CITY,SHANDONG PROVINCE,CHINA
Guangzhou Puho Pharmaceutical Technology Co. Ltd.
Contact:86-20-29848035/29848075
Address:No.166, Chaoyang East Road, Panyu District, Guangzhou City, Guangdong Province
Jiangsu Taihu New Materials Holding Co., Ltd
Contact:+86-519-86160108
Address:Xueyan Town, Changzhou City, Jiangsu Province, 213169, China
Chengdu ZY Biochemical Technology Co., LTD
Contact:0086-28-88680086
Address:170 Qingpu Road, Shouan Town, Pujiang County
Doi:10.1021/ie50517a041
(1953)Doi:10.1021/jo00086a049
(1994)Doi:10.1248/cpb.41.1066
(1993)Doi:10.1016/S0957-4166(97)00434-5
(1997)Doi:10.1039/DT9930002621
(1993)Doi:10.1002/ejoc.201801305
(2018)
