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(+)- and (-)-Mutisianthol : first total synthesis, absolute configuration, and antitumor activity
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
ID
110104
Author(s)
Bianco, Graziela G.; Ferraz, Helena M. C.; Cost, Arinice M.; Costa-Lotufo, Leticia V.; Pessoa, Claudia; de Moraes, Manoel O.; Schrems, Marcus G.; Pfaltz, Andreas; Silva, Luiz F., Jr.
(+)- and (-)-Mutisianthol : first total synthesis, absolute configuration, and antitumor activity
Journal
The journal of organic chemistry
Volume
74
Number
6
Pages / Article-Number
2561-2566
Abstract
The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.
