Volume 29, Issue 31
Natural Products
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ChemInform Abstract: Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions.

Y. KIM

Y. KIM

Dep. Chem. Eng., Calif. Inst. Technol., Pasadena, CA 91125, USA

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R. A. SINGER

R. A. SINGER

Dep. Chem. Eng., Calif. Inst. Technol., Pasadena, CA 91125, USA

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E. M. CARREIRA

E. M. CARREIRA

Dep. Chem. Eng., Calif. Inst. Technol., Pasadena, CA 91125, USA

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First published: 20 June 2010

Abstract

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ChemInform Abstract

Two of three key subunits of macrolactin A (X) containing the desired stereogenic centers are prepared via the title reaction starting from the same precursors (I) and (II) in the presence of either the (R)- or (S)-enantiomeric form of the titanium(IV) catalyst, leading to both enantiomers of (III).The latter are elaborated to give fragments (VII) and (VIII), respectively. Palladium(0)-catalyzed Stille coupling is used to assemble the principal fragments.

chemical structure image

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