C-H-Functionalization logic guides the synthesis of a carbacyclopamine analog

Sebastian Rabe; Johann Moschner; Marina Bantzi; Philipp Heretsch; Athanassios Giannis

doi:10.3762/bjoc.10.161

C-H-Functionalization logic guides the synthesis of a carbacyclopamine analog

Beilstein J Org Chem. 2014 Jul 9:10:1564-9. doi: 10.3762/bjoc.10.161. eCollection 2014.

Authors

Sebastian Rabe¹, Johann Moschner¹, Marina Bantzi¹, Philipp Heretsch², Athanassios Giannis¹

Affiliations

¹ Universität Leipzig, Institut für Organische Chemie, Johannisallee 29, D-04103 Leipzig, Germany.
² Rice University, Department of Chemistry, BioScience Research Collaborative, 6100 Main St., Houston, Texas 77005, United States.

Abstract

The chemical synthesis of carbacyclopamine analog 2, a cyclopamine analog with an all-carbon E-ring, is reported. The use of C-H-functionalization logic and further metal-catalyzed transformations allows for a concise entry to this new class of acid-stable cyclopamine analogs.

Keywords: C–H-functionalization; cyclopamine; hedgehog signaling pathway; natural products; steroidal alkaloids.