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

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.

PMID: 25161712
PMCID: PMC4142839
DOI: 10.3762/bjoc.10.161

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

Sebastian Rabe et al. Beilstein J Org Chem. 2014.

. 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.

PMID: 25161712
PMCID: PMC4142839
DOI: 10.3762/bjoc.10.161

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.

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Figures

**Figure 1**
Structures of cyclopamine (1) and carbacyclopamine analog 2.

**Scheme 1**
Retrosynthetic analysis of carbacyclopamine analog 2.

**Scheme 2**
Synthesis of carbacyclopamine analog 2.

See this image and copyright information in PMC

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

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

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