Synthesis 2002(8): 0981-1003
DOI: 10.1055/s-2002-31946
© Georg Thieme Verlag Stuttgart · New York

The Chemistry and Biology of the Leptomycin Family

Markus Kalesse*, Mathias Christmann
Institut für Chemie/Organische Chemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany
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Further Information

Publication History

Received 22 March 2002
Publication Date:
03 June 2002 (online)


Natural products play a dominant role in providing ligands that interfere with biopolymers such as receptors or enzymes. In many cases the exact mode of action or the targets are not known and synthesis of analogs provides a more detailed insight into the mode of action and helps to identify the protein target. We discuss the synthetic endeavors that led to the synthesis of members of the leptomycin family and will provide a picture of the mode of action.

  • 1 Introduction

  • 2 Synthetic Studies

  • 2.1 Syntheses of the Lactone Fragment (C1-C6)

  • 2.2 Syntheses of Callystatin A

  • 2.3 Syntheses of Ratjadone

  • 2.4 Synthesis of Leptomycin B

  • 3 Biological Evaluation

  • 4 Summary


(-)-Callystatin A was isolated from the marine sponge Callyspongia truncata collected from Goto Islands, Japan. Ratjadone was isolated from the myxobacteria Sorangium cellulosum collected at Cala Ratjada Mallorca, Spain. Leptolstatin was isolated from Streptomyces sp. SAM 1595 Leptomycin was isolated from Streptomyces sp. ATS1287.


Marshall, J. A.; Bourbeau, M. P. J. Org. Chem. 2002, ASAP article.


Attempts to selectively cleave the seemingly more labile TMS group at C17 at a later stage failed an afforded a triol.