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New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment

2003; Wiley; Volume: 2003; Issue: 15 Linguagem: Inglês

10.1002/ejoc.200300255

1434-193X

Véronique Michelet, Kouacou Adiey, Suzelle Tanier, Gilles Dujardin, Jean‐Pierre Genêt,

Microbial Natural Products and Biosynthesis

Abstract Stereoselective ethynylation of functionalized β‐C‐glycosyl aldehydes has been achieved with various organometallic alkynes. The diastereoselectivity is highly dependent on the organometallic alkyne and on the functionalization on the C‐6 position of the glycoside. The stereoselective reaction conducted with ester‐functionalized aldehyde, followed by Mitsunobu reaction and two Pd‐catalyzed regio‐ stereo‐ and enantioselective alkylations afforded the “western” part of ambruticin. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)