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)

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements