TY - JOUR A1 - Raffier, Ludovic A1 - Piva, Olivier T1 - Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H JF - Beilstein Journal of Organic Chemistry PY - 2011/// VL - 7 SP - 151 EP - 155 SN - 1860-5397 DO - 10.3762/bjoc.7.21 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.7.21 KW - amide KW - diastereoselective protonation KW - dienol KW - isomerisation KW - Wittig reaction N2 - The asymmetric synthesis of gymnastatin H has been achieved by using the photoisomerisation of a conjugated ester to its β,γ-unsaturated isomer through the protonation of a in situ generated dienol as key step. Thanks to diacetone D-glucose used as a chiral alkoxy group, the protonation occurred well onto one of the two diastereotopic faces with very high yields and selectivities. Moreover, by this way the configuration of the C-6 centre of the target molecule was controlled. ER -