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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)

No abstract

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Carbohydrates Carbohydrates U 0500 New Aspects in the Stereoselective Ethynylation of β-C-Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment. -The stereoselective outcome of the ethynylation strongly depends on the nature of organometallic alkyne and the C-6 substituent of the glycoside. The method is applied to the synthesis of the C1-C13 unit (XI) of ambruticin. -(MICHELET*, V.; ADIEY, K.; TANIER, S.; DUJARDIN, G.; GENET, J.-P.; Eur.