Total synthesis of (+/-)-(1 beta,4 beta,4a beta,8a alpha)-4,8-a-dimethyl-octahydro-naphthalene-1,4a(2H)-diol

The first total synthesis of (+/-)-(1,4,4a,8a)-4,8a-dimethylocta-hydronaphthalene-1,4a(2H)-diol (1), a degraded sesquiterpene isolated from a fermentation broth of Streptomyces albolongus, has been achieved via three different synthetic approaches (13-15 steps) starting from racemic Wieland-Miescher...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 10; pp. 1719 - 1723
Main Authors Liu, Qingyin, Han, Li, Qin, Bing, Mu, Yu, Guan, Peipei, Wang, Songyao, Huang, Xueshi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.05.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
(-)-GEOSMIN
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Summary:The first total synthesis of (+/-)-(1,4,4a,8a)-4,8a-dimethylocta-hydronaphthalene-1,4a(2H)-diol (1), a degraded sesquiterpene isolated from a fermentation broth of Streptomyces albolongus, has been achieved via three different synthetic approaches (13-15 steps) starting from racemic Wieland-Miescher ketone (2). The configuration of hydroxyl groups at C-1 and C-4a in 1 was availably managed using the Mitsunobu reaction and stereo- and regioselective epoxidation. Moreover, the syntheses of configuration isomers 12, 17, 45 and 54 were also described in the present study.
ISSN:2052-4129
DOI:10.1039/c8qo00225h