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(+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
- Source :
- The Journal of Organic Chemistry. 74:2561-2566
- Publication Year :
- 2009
- Publisher :
- American Chemical Society (ACS), 2009.
-
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.
- Subjects :
- Biological Products
Stereochemistry
Organic Chemistry
Asymmetric hydrogenation
Enantioselective synthesis
Absolute configuration
Total synthesis
Antineoplastic Agents
Stereoisomerism
Alkenes
Anisoles
Chemical synthesis
chemistry.chemical_compound
chemistry
Cell Line, Tumor
Yield (chemistry)
Mutisianthol
Humans
Hydrogenation
Drug Screening Assays, Antitumor
Enantiomer
Sesquiterpenes
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 74
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....5bf209131c1942e274635f50b7553b5b