Total synthesis of diazonamide A

Robert R. Knowles; Joseph Carpenter; Simon B. Blakey; Akio Kayano; Ian K. Mangion; Christopher J. Sinz; David W.C. MacMillan

doi:10.1039/c0sc00577k

Total synthesis of diazonamide A

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

Research output: Contribution to journal › Article › peer-review

131 Scopus citations

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.

Original language	English (US)
Pages (from-to)	308-311
Number of pages	4
Journal	Chemical Science
Volume	2
Issue number	2
DOIs	https://doi.org/10.1039/c0sc00577k
State	Published - 2011

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/c0sc00577k

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title = "Total synthesis of diazonamide A",

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.",

author = "Knowles, \{Robert R.\} and Joseph Carpenter and Blakey, \{Simon B.\} and Akio Kayano and Mangion, \{Ian K.\} and Sinz, \{Christopher J.\} and MacMillan, \{David W.C.\}",

year = "2011",

doi = "10.1039/c0sc00577k",

language = "English (US)",

volume = "2",

pages = "308--311",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Total synthesis of diazonamide A

AU - Knowles, Robert R.

AU - Carpenter, Joseph

AU - Blakey, Simon B.

AU - Kayano, Akio

AU - Mangion, Ian K.

AU - Sinz, Christopher J.

AU - MacMillan, David W.C.

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/79955636572

UR - https://www.scopus.com/pages/publications/79955636572#tab=citedBy

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DO - 10.1039/c0sc00577k

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SN - 2041-6520

VL - 2

SP - 308

EP - 311

JO - Chemical Science

JF - Chemical Science

IS - 2

ER -

Total synthesis of diazonamide A

Abstract

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