Stereoselective total synthesis of nemorosone

The Journal of Organic Chemistry
Masahiro UwamoriMasahisa Nakada

Abstract

The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

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Citations

Feb 7, 2013·The Journal of Antibiotics·Masahiro Uwamori, Masahisa Nakada
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Aug 8, 2015·Journal of the American Chemical Society·Chi P Ting, Thomas J Maimone
Sep 5, 2012·Bioorganic & Medicinal Chemistry Letters·Nigel S SimpkinsRobert Wolf
Jan 26, 2020·Nature Communications·Xingyu ShenThomas J Maimone
Jan 14, 2017·European Journal of Organic Chemistry·Mikayo HayashiJohn A Porco
Sep 24, 2020·Angewandte Chemie·Jonathan H BoyceJohn A Porco
Jul 28, 2021·The Journal of Organic Chemistry·George KwesigaBernd Schmidt
Dec 29, 2012·Journal of the American Chemical Society·Brian A SparlingMatthew D Shair
Aug 29, 2014·Journal of the American Chemical Society·Max R FriedfeldPaul J Chirik
Jul 26, 2014·Journal of the American Chemical Society·Alexander J GrenningJohn A Porco
Aug 29, 2018·Organic Letters·Mario Kock, Thomas Lindel
Feb 21, 2018·Chemical Reviews·Xing-Wei YangGang Xu
Jul 1, 2015·Organic Letters·Brian A SparlingMatthew D Shair
Sep 6, 2014·Organic Letters·Kenji UsuiAnd Masahisa Nakada
May 8, 2018·The Journal of Organic Chemistry·Gabriel Bellavance, Louis Barriault

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