10.1021/ol025683x.s001 Paolo Celestini Paolo Celestini Bruno Danieli Bruno Danieli Giordano Lesma Giordano Lesma Alessandro Sacchetti Alessandro Sacchetti Alessandra Silvani Alessandra Silvani Daniele Passarella Daniele Passarella Andrea Virdis Andrea Virdis <i>trans</i>-6-Aminocyclohept-3-enols, a New Designed Polyfunctionalized Chiral Building Block for the Asymmetric Synthesis of 2-Substituted-4-hydroxypiperidines American Chemical Society 2002 ci Aminocyclohept Efficient enantiomeric forms cyclohept New enzymatically polyfunctionalized chiral building blocks enantioselective syntheses Substituted ent hydroxypipecolic Asymmetric Synthesis Polyfunctionalized Chiral Building Block piperidine alkaloids synthesis piperidines 3 monoacetate tran yield acid 2002-03-23 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/_i_trans_i_-6-Aminocyclohept-3-enols_a_New_Designed_Polyfunctionalized_Chiral_Building_Block_for_the_Asymmetric_Synthesis_of_2-Substituted-4-hydroxypiperidines/3742368 <i>trans</i>-6-Aminocyclohept-3-enols <b>18</b> and <i>ent</i>-<b>18</b> are new designed polyfunctionalized chiral building blocks for piperidine alkaloids synthesis and are prepared in high yields from the enzymatically derived cyclohept-3-ene-1,6-diol monoacetate (−)-<b>8</b>. Efficient highly enantioselective syntheses of <i>cis</i>-4-hydroxypipecolic acid (<b>1</b>) and piperidines <b>3</b> and <b>4</b>, in both enantiomeric forms, are described.