Synthesis 2018; 50(08): 1587-1600
DOI: 10.1055/s-0036-1591965
short review
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-Nor-D-homo-steroidal Alkaloids and Their Derivatives

Farnoush Mousavizadeh
University of Leipzig, Institute for Organic Chemistry, Johannisallee 29, 04103 Leipzig, Germany   Email: [email protected]
,
Daniel Meyer
University of Leipzig, Institute for Organic Chemistry, Johannisallee 29, 04103 Leipzig, Germany   Email: [email protected]
,
University of Leipzig, Institute for Organic Chemistry, Johannisallee 29, 04103 Leipzig, Germany   Email: [email protected]
› Author Affiliations
Deutsche Forschungsgemeinschaft (Grant number GI 204/8-1).
Further Information

Publication History

Received: 02 January 2018

Accepted after revision: 27 February 2018

Publication Date:
21 March 2018 (online)


§ Both authors contributed equally to this work.

Abstract

The C-nor-D-homo-steroidal alkaloid cyclopamine was discovered in the 1969 and in 2000 it was shown to act as an inhibitor of the hedgehog signaling (Hh) pathway, which is aberrantly activated in some tumors. Subsequently it was revealed that this natural occurring alkaloid has also antidiabetic and antiviral properties. In this review we present syntheses of selected C-nor-D-homo-steroidal alkaloids and their analogues and also discuss a general access to C-nor-D-homo-steroids. Some historical as well as biomedical aspects are also presented.

1 Introduction

2 Total Synthesis of Cyclopamine

2.1 Synthesis of exo-Cyclopamine and Further Cyclopamine Analogues

2.2 Synthesis of a Carbacyclopamine Analogue

3 D-Homocyclopamine: Saridegib (IPI-926)

4 Synthesis of Nakiterpiosin

5 Lewis Acid Mediated Nazarov Cyclization as a Versatile Method for C-Nor-D-homo-steroid Synthesis

6 Conclusion

 
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