Total synthesis of hirsutellone B via Ullmann-type direct 13-membered macrocyclization

Hiromi Uchiro; Ryo Kato; Yuuki Arai; Miki Hasegawa; Yu Kobayakawa

doi:10.1021/ol202748e

Total synthesis of hirsutellone B via Ullmann-type direct 13-membered macrocyclization

Org Lett. 2011 Dec 2;13(23):6268-71. doi: 10.1021/ol202748e. Epub 2011 Oct 31.

Authors

Hiromi Uchiro¹, Ryo Kato, Yuuki Arai, Miki Hasegawa, Yu Kobayakawa

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan. uchiro@rs.noda.tus.ac.jp

PMID: 22040033
DOI: 10.1021/ol202748e

Abstract

Total synthesis of Hirsutellone B has been achieved by a convergent synthetic strategy. This synthesis features direct construction of the highly strained 13-membered macrocycle of Hirsutellone B utilizing the Ullmann-type reaction. To the best of our knowledge, this is the first application of macrocyclization utilizing an intramolecular Ullmann-type reaction between an aliphatic alcohol and aryl halide.

MeSH terms

Antitubercular Agents / chemical synthesis*
Antitubercular Agents / chemistry
Antitubercular Agents / pharmacology
Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / pharmacology
Molecular Structure
Mycobacterium tuberculosis / drug effects
Stereoisomerism

Substances

Antitubercular Agents
Heterocyclic Compounds, 4 or More Rings
hirsutellone B