To conclude, a convergent total synthesis of (-)cyclopamine (1) was achieved with a 15-step LLS (62% ideality) from (S)-Wieland-Miescher ketone. Unlike the semisynthetic routes which predate this disclosure, the strategy outlined herein should be amenable to exploring deep-seated structural modifications for further SAR studies of this promising class of natural products. Key areas for improvement for which there are methodological gaps include a more direct conversion of 18 to 20 (see SI for discussion) and a more concise fragment coupling that can minimize PGmanipulations. That said, notable features of this synthesis include rapid stereocontrolled access to similarly sized coupling fragments, namely the streamlined ABC-ring synthesis through annulation/CuH reduction and an unusually concise furanbased access to the key EF ring system via AAA/aza-Michael/halocyclization. Furthermore, the exquisite stereocontrol exhibited in the fragment coupling/strained THF ring formation prior to the high-yielding RCM cyclization represents a bold yet effective means of accessing 1.