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. 2011 May 6;13(9):2484-7.
doi: 10.1021/ol200735r. Epub 2011 Apr 6.

C(21)-C(40) of tetrafibricin via metal catalysis: beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles

Esa T T Kumpulainen  1 , Byungsoo Kang, Michael J Krische
Affiliations

C(21)-C(40) of tetrafibricin via metal catalysis: beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles

Esa T T Kumpulainen et al. Org Lett. .

Abstract

The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer hydrogenative carbonyl allylation and 2 C═C bonds are formed via Grubbs olefin cross-metathesis.

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Figures

Scheme 1
Scheme 1
Retrosynthetic analysis of the fibrinogen receptor inhibitor tetrafibricin.
Scheme 2
Scheme 2
Enantioselective allylation of N-Boc-4-aminobutan-1-ol 1 with recovery of the iridium catalyst.
Scheme 3
Scheme 3
Conversion of homoallylic alcohol 2 to 1,5-enediol 6.
Scheme 4
Scheme 4
Conversion of 1,3-propanediol to 1,3-polyol 14.
Scheme 5
Scheme 5
Cross-metathesis to form the C(21)-C(40) fragment of tetrafibricin.
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