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. 2010 Sep 3;12(17):3752-5.
doi: 10.1021/ol101340n.

Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence

Dong Gao  1 , George A O'Doherty
Affiliations

Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence

Dong Gao et al. Org Lett. .

Abstract

A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.

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Figures

Figure 1
Figure 1
Fostriecin (1, CI-920)
Figure 2
Figure 2
Related natural products to fostriecin
Scheme 1
Scheme 1
Fostriecin (1) retrosynthesis
Scheme 2
Scheme 2
Synthesis of trieneoate 10
Scheme 3
Scheme 3
Asymmetric hydration and oxidation of triene 10
Scheme 4
Scheme 4
Substrate optimization for the trans-hydroboration
Scheme 5
Scheme 5
Trans-hydroboration and pyranone installation
Scheme 6
Scheme 6
Fostriecin End-Game
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