(+)- 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.
Bianco
Graziela G
GG
Department of Chemistry, Institute of Chemistry, University of Sao Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 Sao Paulo SP, Brazil.
Ferraz
Helena M C
HM
Costa
Arinice M
AM
Costa-Lotufo
Letícia V
LV
Pessoa
Cláudia
C
de Moraes
Manoel O
MO
Schrems
Marcus G
MG
Pfaltz
Andreas
A
Silva
Luiz F
LF
D000475:Alkenes / Q000737:chemistry; D000840:Anisoles / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006865:Hydrogenation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000475:Alkenes; D000840:Anisoles; D000970:Antineoplastic Agents; D001688:Biological Products; D012717:Sesquiterpenes; C540246:mutisianthol; C428434:2-methylanisole