Issue 13, 2010
From the journal:

Chemical Communications

Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain viaZr-catalyzed asymmetric carboalumination of alkenes (ZACA)†‡

Emmanuel Pitsinos,*a   Nikolaos Athinaios,a   Zhaoqing Xu,b   Guangwei Wangb  and  Ei-ichi Negishi*b  

* Corresponding authors

a Laboratory of Natural Products Synthesis & Bioorganic Chemistry, Institute of Physical Chemistry, NCSR “DEMOKRITOS”, P.O. Box 60228, GR 153 10, Aghia Paraskevi, Greece
E-mail: pitsinos@chem.demokritos.gr

b Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA
E-mail: negishi@purdue.edu

Abstract

(+)-Scyphostatin (1) was synthesized via (i) construction of a side-chain 3b of ≥98% purity in 19% yield in eleven steps featuring ZACA reaction, Negishi coupling, and HWE olefination, (ii) an asymmetric synthesis of a fully protected core 4 from 10a, and (iii) a three-step assembly of 1 in 42% yield.

Graphical abstract: Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)

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Article information

DOI
https://doi.org/10.1039/B920261G
Article type
Communication
Submitted
29 Sep 2009
Accepted
09 Feb 2010
First published
23 Feb 2010

Chem. Commun., 2010,46, 2200-2202

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Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)

E. Pitsinos, N. Athinaios, Z. Xu, G. Wang and E. Negishi, Chem. Commun., 2010, 46, 2200 DOI: 10.1039/B920261G

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