Synlett 2012; 23(16): 2298-2310
DOI: 10.1055/s-0031-1290460
© Georg Thieme Verlag Stuttgart · New York

The Chemistry and Biology of Nakiterpiosin – C-nor-D-Homosteroids

Shuanhu Gaoa, Qiaoling Wanga, Gelin Wanga, Brett Lomenickb, Jie Liuc, Chih-Wei Fand, Lih-Wen Dengc, Jing Huangb, Lawrence Lumd, Chuo Chen*a
  • aDepartment of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
  • bDepartment of Molecular and Medical Pharmacology, University of California, Los Angeles, California 90095, USA
  • cDepartment of Biochemistry, Yong Loo Lin School of Medicine, National University of Singapore, Singapore
  • dDepartment of Cell Biology, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA, Fax: +1(214)6480320   Email:
Further Information

Publication History

Received: 18 May 2012

Accepted: 17 July 2012

Publication Date:
14 September 2012 (eFirst)


Isolated from the sponge Terpios hoshinota that causes coral black disease, nakiterpiosin was the first C-nor-D-homosteroid discovered from a marine source. We provide in this account an overview of the chemistry and biology of this natural product. We also include a short history of the synthesis of C-nor-D-homosteroids and the results of some unpublished biological studies of nakiterpiosin.

1 Introduction

2 Synthesis of C-nor-D-Homosteroids

2.1 The Biomimetic Approaches

2.2 The Ring-by-Ring Approaches

2.3 Miscellaneous Approaches

3 Structural Revision of Nakiterpiosin

4 Synthesis of Nakiterpiosin

5 Biology of Nakiterpiosin

6 Conclusion