(+)- and (-)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity

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.

FAPESP

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

CNPq

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Swiss National Science Foundation (SNSF)

Swiss National Science Foundation (NSF)

Federal Commission for Technology and Innovation (KTI)

Federal Commission for Technology and Innovation (KTI)