(-)-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.
Asymmetric Total Synthesis of (−)-Juvabione via Sequential Ir-Catalyzed Hydrogenations / Zheng, Jia; Margarita, Cristiana; Krajangsri, Suppachai; Andersson, Pher G.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 20:18(2018), pp. 5676-5679. [10.1021/acs.orglett.8b02405]
Asymmetric Total Synthesis of (−)-Juvabione via Sequential Ir-Catalyzed Hydrogenations
Margarita, CristianaSecondo
;
2018
Abstract
(-)-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
