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

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Article information

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

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

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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

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