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

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

Shuanhu Gao
a   Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
,
Qiaoling Wang
a   Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
,
Gelin Wang
a   Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
,
Brett Lomenick
b   Department of Molecular and Medical Pharmacology, University of California, Los Angeles, California 90095, USA
,
Jie Liu
c   Department of Biochemistry, Yong Loo Lin School of Medicine, National University of Singapore, Singapore
,
Chih-Wei Fan
d   Department of Cell Biology, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA, Fax: +1(214)6480320   Email: Chuo.Chen@UTSouthwestern.edu
,
Lih-Wen Deng
c   Department of Biochemistry, Yong Loo Lin School of Medicine, National University of Singapore, Singapore
,
Jing Huang
b   Department of Molecular and Medical Pharmacology, University of California, Los Angeles, California 90095, USA
,
Lawrence Lum
d   Department of Cell Biology, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA, Fax: +1(214)6480320   Email: Chuo.Chen@UTSouthwestern.edu
,
Chuo Chen*
a   Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA
› Author Affiliations
Further Information

Publication History

Received: 18 May 2012

Accepted after revision: 17 July 2012

Publication Date:
14 September 2012 (online)


Abstract

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 We also include a short history of the synthesis of C-nor-D-homosteroids and the results of some unpublished biological studies of nakiterpiosin.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

 
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