Studies on the total synthesis of lactonamycin: construction of model ABCD ring systems

The Journal of Organic Chemistry
David A HendersonAnthony G M Barrett

Abstract

Model studies on the synthesis of the tetracyclic ABCD ring system of lactonamycin (1) are described. The key step involved the double Michael addition reaction of alcohol 8 to propynoate esters to produce the BCD units 13 and 14 of the target 1. Alternatively, double Michael addition of alcohol 8 to di-tert-butyl acetylenedcarboxylate gave the corresponding BCD ring systems 36 and 37. Acid-mediated hydrolysis of the dihydroquinone monoketal units of 13 and 14 and 36 and 37 in the presence of air gave the corresponding quinones 7 and 39. These were converted into the tetracyclic ABCD units 6, 26a, 40, and 42 of lactonamycin (1) by either dihydroxylation or epoxidation and acid-catalyzed lactonization.

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Citations

Oct 3, 2009·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Toshifumi Dohi
Dec 29, 2016·The Journal of Organic Chemistry·Zhilong Li, Rongbiao Tong
Apr 27, 2017·Organic Letters·Philip J ParsonsAndrew J P White
Jul 28, 2016·Angewandte Chemie·Shogo KamoKazunori Tsubaki
Mar 29, 2014·Organic & Biomolecular Chemistry·Kathryn A Punch, Matthew J Piggott
Apr 9, 2008·Angewandte Chemie·Toshifumi DohiYasuyuki Kita
Jul 6, 2011·Organic & Biomolecular Chemistry·Kenichi KobayashiOsamu Tamura
Jan 29, 2011·Angewandte Chemie·Alexander Duschek, Stefan F Kirsch
Sep 6, 2011·Organic & Biomolecular Chemistry·Toshifumi DohiYasuyuki Kita
Oct 5, 2019·Chemical Science·Yinan ZhangJon S Thorson
Aug 14, 2010·The Journal of Organic Chemistry·Kana WatanabeMasaya Nakata
Mar 1, 2013·Journal of the American Chemical Society·Toshifumi DohiYasuyuki Kita
Oct 10, 2006·The Journal of Organic Chemistry·Hermut WehlanAnthony G M Barrett

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