Asymmetric Total Synthesis of (−)-Juvabione via Sequential Ir-Catalyzed Hydrogenations | Zendy

Jia Zheng | Zendy; Cristiana Margarita | Zendy; Suppachai Krajangsri | Zendy; Pher G. Andersson | Zendy

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Asymmetric Total Synthesis of (−)-Juvabione via Sequential Ir-Catalyzed Hydrogenations

Author(s) -

Jia Zheng,

Cristiana Margarita,

Suppachai Krajangsri,

Pher G. Andersson

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b02405

Subject(s) - stereocenter , chemistry , yield (engineering) , sesquiterpene , catalysis , total synthesis , stereochemistry , combinatorial chemistry , diene , organic chemistry , enantioselective synthesis , materials science , natural rubber , metallurgy

(-)-Juvabione, a natural sesquiterpene exhibiting juvenile insect hormone activity, was synthesized constructing the two adjacent stereogenic centers via sequential Ir-catalyzed hydrogenations. The first center is generated by hydrogenation of a styrene-type double bond (99% ee). The successive monohydrogenation of a diene intermediate constitutes the key step, granting high levels of regio- and stereocontrol (94:6 dr). This novel strategy allowed the preparation of (-)-juvabione from simple starting materials in 9 steps and 17% total yield.

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