1131235-80-7Relevant articles and documents
(+)- And (-)-mutisianthol: First total synthesis, absolute configuration, and antitumor activity
Bianco, Graziela G.,Ferraz, Helena M. C.,Costas, Arinice M.,Costa-Lotufo, Leticia V.,Pessoa, Claudia,De Moraes, Manoel O.,Schreins, Marcus G.,Pfaltz, Andreas,Silva Jr., Luiz F.
, p. 2561 - 2566 (2009)
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 (15,37?). 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.
