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 MoreChengdu ZY Biochemical Technology Co., LTD
Contact:0086-28-88680086
Address:170 Qingpu Road, Shouan Town, Pujiang County
Suzhou Tianma Specialty Chemicals Co.,Ltd
Contact:+86-512-68090577
Address:#199, Huayuan Rd, Mudu, Suzhou, Jiangsu, CHINA
website:http://www.jairadhesales.com
Contact:0091-79-26431096
Address:309 Harikrupa Tower,Nr old Sharda Mandir Char Rasta,Ellisbridge
Contact:+86-570-4336358
Address:No.87 Building,Tianqian,Sidu Town
Shandong Wanda Organosilicon New Material Co., Ltd
Contact:+86-21-54177116;54302881
Address:R1318 Greenland No. 3 Lane 58 Xinjian East Rd., Minhang
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)
