PMID: 10774027Apr 25, 2000Paper

First atropo-divergent total synthesis of the antimalarial korupensamines A and B by the "lactone method"

The Journal of Organic Chemistry
G BringmannR Götz

Abstract

The stereoselective total synthesis of the antimalarial korupensamines A (1a) and B (1b) by application of the "lactone method" is described. Key steps of this first atropo-selective access to 5,8'-coupled naphthylisoquinoline alkaloids were the regioselective intramolecular coupling of ester 8 to give the configurationally labile lactone-bridged biaryl 9 and its atropisomer-selective cleavage with a variety of chiral and achiral H-nucleophiles, yielding the configurationally stable P-diol 10a or, optionally, the M-product 10b. From the axially chiral phenylisoquinolines thus obtained atropo-diastereodivergently, the authentic natural naphthylisoquinolines with the respective axial configurations, korupensamines A (1a) and B (1b), were obtained by completion of the second naphthalene ring, starting from the previous "bridgehead" C1 unit.

Citations

Mar 16, 2006·Chemical Communications : Chem Comm·Louis-Charles Campeau, Keith Fagnou
May 5, 2017·Angewandte Chemie·Hamish D ToopJonathan C Morris
Aug 24, 2005·Angewandte Chemie·Gerhard BringmannMatthias Breuning
Dec 16, 2004·Chemical Communications : Chem Comm·Marc LafranceKeith Fagnou
Jun 9, 2016·Chemistry : a European Journal·Gerhard BringmannRaina Seupel
May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Jan 2, 2010·Journal of the American Chemical Society·Gerhard BringmannFrank Meyer
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Garazi UrgoitiaRaul SanMartin
Sep 21, 2010·Journal of the American Chemical Society·Shenlin HuangBruce H Lipshutz
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Oct 24, 2013·Journal of the American Chemical Society·Guangqing XuWenjun Tang
Sep 15, 2020·The Journal of Organic Chemistry·Young-In JoCheol-Hong Cheon
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Aug 3, 2002·The Journal of Organic Chemistry·Gerhard BringmannBerhanu M Abegaz
Jun 5, 2004·The Journal of Organic Chemistry·Takashi WatanabeMotokazu Uemura

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