Crinipellins are the only natural products with AB tetraquinane framework. The highly congested structure with eight stereogenic centers and highly reactive functional groups make it a great challenge for total synthesis. The total synthesis of crinipellin A and B was achieved using tandem cycloaddition reaction strategies via a trimethylenemethane (TMM) diyl-mediated [2+3] cycloaddition reaction. A formal total synthesis of crinipellin B preceded the asymmetric total synthesis of crinipellin A through the tandem [2+3] cycloaddition reaction of a diazoallenyl substrate containing a cyclopentane ring. The substrate for the cycloaddition reaction was prepared enantioselectively and subsequent selective functional group manipulation completed the first asymmetric total synthesis of crinipellin A.