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New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment
Author(s) -
Michelet Véronique,
Adiey Kouacou,
Tanier Suzelle,
Dujardin Gilles,
Genêt JeanPierre
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300255
Subject(s) - chemistry , stereoselectivity , aldehyde , enantioselective synthesis , alkyne , glycosyl , glycoside , organic chemistry , stereochemistry , catalysis , combinatorial chemistry
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)