Issue 45, 2013
From the journal:

Chemical Communications

Total synthesis of (−)-kaitocephalin†

Wonchul Lee,a   Joo-Hack Younb  and  Sung Ho Kang*a  

* Corresponding authors

a MIRC, Department of Chemistry, KAIST, Daejeon 305-701, Korea
E-mail: shkang@kaist.ac.kr
Fax: +82-42-350-2810
Tel: +82-42-350-2825

b Department of Chemical and Biochemical Engineering, Sun Moon University, Asan-si, Chungnam 336-840, Korea

Abstract

(−)-Kaitocephalin has been synthesized. With the C9 stereocenter from Garner's aldehyde, the C4 quaternary carbon was installed by the desymmetrization of the Cbz-protected serinol. The remaining stereogenic centers were generated through mercuriocyclization, epoxidation and regioselective epoxide opening, in which the quaternary carbon most likely played crucial roles in the stereoinduction.

Graphical abstract: Total synthesis of (−)-kaitocephalin

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Article information

DOI
https://doi.org/10.1039/C3CC42365D
Article type
Communication
Submitted
01 Apr 2013
Accepted
17 Apr 2013
First published
30 Apr 2013

Chem. Commun., 2013,49, 5231-5233

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Total synthesis of (−)-kaitocephalin

W. Lee, J. Youn and S. H. Kang, Chem. Commun., 2013, 49, 5231 DOI: 10.1039/C3CC42365D

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