Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

Noriaki Itagaki; Yoshiharu Iwabuchi

doi:10.1039/B616641E

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Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation†

Noriaki Itagaki^a and Yoshiharu Iwabuchi*^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan
E-mail: iwabuchi@mail.pharm.tohoku.ac.jp
Fax: +81 22 795 6845
Tel: +81 22 795 6845

Abstract

(+)-Juvabione, a natural sesquiterpene exhibiting insect juvenile hormone activity, has been synthesized from σ-symmetric 4-(2-formylethyl)cyclohexanone by employing organocatalytic asymmetric aldolisation and Norrish I-type fragmentation as the key steps.

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Supplementary files

Experimental details and spectroscopic data (IR, ¹H NMR, ¹³C NMR, and HRMS of all new isolable compounds except 3, 13, and 17, and ¹H NMR and ¹³C NMR of 13) PDF (2201K)

Article information

DOI: https://doi.org/10.1039/B616641E
Article type: Communication
Submitted: 14 Nov 2006
Accepted: 18 Dec 2006
First published: 09 Jan 2007

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Chem. Commun., 2007, 1175-1176

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Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

N. Itagaki and Y. Iwabuchi, Chem. Commun., 2007, 1175 DOI: 10.1039/B616641E

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Chemical Communications

Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation†

Abstract

Supplementary files

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Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

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