The thermally induced electrocyclic ring -opening of C2 -symmetric (meso) 6,6-dibromobicyclo[3.1.0]hexanes such as 10 in the presence of the chiral, nonracemic 1 -amine 28 afforded a ca. 1:1 mixture of the diastereoisomeric and chromatographically separable amino-2-bromo-2-cyclohexenes 37 (42%) and 38 (45%). Each of these was elaborated over 13 steps, including Suzuki Miyaura cross coupling, radical cyclization, and Pictet Spengler reactions, into (-)- or (+)-crinane (1 or ent-1, respectively). Variations on these protocols were applied to the total syntheses of (+)- and (-)-1-hydroxyvattitine [ (+)- and (-)-3], (+)- and (-)- bulbisp ermine [(+)-and (-)-4], (+)- and (-)- haemanthamine [(+)-and (-)-5], (+)-and (-)-pretazettine [(+)-and (-)-6], and (+)-and (-)-tazettine [(+)-and (-)-7] as well as (-)-hamayne [(-)-8] and (-)-apohaemanthamine [(-)-9]. A number of these alkaloids were synthesized for the first time.