Issue 2, 2011
From the journal:

Chemical Science

Total synthesis of diazonamide A†

Robert R. Knowles,a   Joseph Carpenter,a   Simon B. Blakey,a   Akio Kayano,a   Ian K. Mangion,a   Christopher J. Sinza  and  David W. C. MacMillan*a  

* Corresponding authors

a Merck Center for Catalysis at Princeton University, Princeton, New Jersey, USA
E-mail: dmacmill@princeton.edu
Fax: +1 609 2585922
Tel: +1 609 2582254

Abstract

A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation–cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.

Graphical abstract: Total synthesis of diazonamide A

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0SC00577K
Article type
Edge Article
Submitted
17 noy 2010
Accepted
02 dek 2010
First published
24 dek 2010

Chem. Sci., 2011,2, 308-311

Permissions

Request permissions

Total synthesis of diazonamide A

R. R. Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J. Sinz and D. W. C. MacMillan, Chem. Sci., 2011, 2, 308 DOI: 10.1039/C0SC00577K

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