Optically lively aldehyde 9 was also prepared in 99 % ee in exam help similar fashion19 using exam help chiral amine base for the cyanation response,20 but we chose exam pursue the synthesis of the metathesis precursors with the racemic aldehyde examination widen the array of taxoids generated, and exam study the have an effect on of the stereochemistry of the precursor on the RCM response effect. a DMP, CH2Cl2; b Zn, NH4Cl, prenyl bromide, 99 % over 2 steps; c exam help DMP, CH2Cl2, 95 %; d TMSCN, DABCO, CH2Cl2; e DIBAL‐H, CH2Cl2; SiO2 58 % over 2 steps. In order examination test the important thing metathesis reaction, we decided examination use exam help 7‐deoxy C ring as exam help coupling partner within the Shapiro response. It is worth noting that elimination of the practical group at C7 in Taxol did not result in exam help gigantic loss of bioactivity. 21 When hydrazone 12 Scheme 3, prepared in 76 % yield from the corresponding known ketone,22 was submitted exam tBuLi for the Shapiro coupling, only degradation was observed. 23 We surmised that this was due examination the deprotonation at the allylic position, and thus the alkene was masked as exam help protected primary alcohol.
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