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. 2009 Nov 5;11(21):5086-8.
doi: 10.1021/ol902154p.

Enantioselective formal total synthesis of (+)-aspergillide C

Joseph D Panarese  1 , Stephen P Waters
Affiliations

Enantioselective formal total synthesis of (+)-aspergillide C

Joseph D Panarese et al. Org Lett. .

Abstract

An enantioselective formal total synthesis of the cytotoxic macrolide (+)-aspergillide C has been accomplished from (S)-(-)-glyceraldehyde acetonide and the Danishefsky-Kitahara diene. Strategic transformations include a hetero Diels-Alder reaction, Ferrier-type addition, and palladium-catalyzed oxidative lactonization to set key stereocenters within the dihydropyran core, followed by fragment coupling via (E)-selective Julia-Kocienski olefination.

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Figures

Figure 1
Figure 1
Confirmed structures of aspergillides A–C.
Scheme 1
Scheme 1
Retrosynthetic Analysis of (+)-Aspergillide C
Scheme 2
Scheme 2
Preparation of Lactone (+)-13
Scheme 3
Scheme 3
Preparation of Sulfone Fragment (+)-18
Scheme 4
Scheme 4
Fragment Coupling via Modified Julia Olefination
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References

    1. Kito K, Ookura R, Yoshida S, Namikoshi M, Ooi T, Kusumi T. Org. Lett. 2008;10:225–228. - PubMed
    1. Hande SM, Uenishi J. Tetrahedron Lett. 2009;50:189–192.
    1. Ookura R, Kito K, Saito Y, Kusumi T, Ooi T. Chem. Lett. 2009;38:384.

    1. Total syntheses of aspergillide B subsequent to ref. : Liu J, Xu K, He J, Zhang L, Pan X, She X. J. Org. Chem. 2009;74:5063–5066. Diaz-Oltra S, Angulo-Pachon CA, Kneeteman MN, Murga J, Carda M, Marco JA. Tetrahedron Lett. 2009;50:3783–3785. Nagasawa T, Kuwahara S. Biosci. Biotechnol. Biochem. 2009;73:1893–1894.

    1. Total synthesis of aspergillide C: Kuwahara S, Nagasawa T. Org. Lett. 2009;11:761–764.

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