Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel-Crafts type cyclizationCCDC 1446962 (13) and 1419158 (14). For crystallographic data in CIF or other electronic format see DOI: 10.1039/c6cc03764j

Enantioselective total synthesis of (+)-Lingzhiol has been achieved. It is the first example of in tandem semipinacol rearrangement reactions, the migrated aryl group further reacting with the carbonyl oxonium electrophile to furnish a polycyclic skeleton. Our synthesis involves 13 steps and proceed...

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Main Authors Chen, Dong, Xu, Wen-Dan, Liu, Hao-Miao, Li, Ming-Ming, Yan, Yong-Min, Li, Xiao-Nian, Li, Yan, Cheng, Yong-Xian, Qin, Hong-Bo
Format Journal Article
Published 30.06.2016
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Summary:Enantioselective total synthesis of (+)-Lingzhiol has been achieved. It is the first example of in tandem semipinacol rearrangement reactions, the migrated aryl group further reacting with the carbonyl oxonium electrophile to furnish a polycyclic skeleton. Our synthesis involves 13 steps and proceeds in 6% overall yield. Enantioselective total synthesis of (+)-Lingzhiol has been achieved. Tandem semipinacol rearrangement/lactone formation/Friedel-Crafts cyclization/elimination reaction was developed to construct the four-ring core skeleton.
Bibliography:CCDC
13
1446962
1419158
14
and
For crystallographic data in CIF or other electronic format see DOI
(
10.1039/c6cc03764j
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc03764j