1170034-89-5Relevant academic research and scientific papers
Total synthesis of altenusin and alterlactone
Cudaj, Judith,Podlech, Joachim
, p. 371 - 374 (2012/03/27)
The resorcylic lactone alterlactone, a mycotoxin produced by alternaria sp., was synthesized for the first time. The total synthesis was achieved in nine steps with 69% yield starting with acetal-protected phloroglucinic acid and 6-bromopiperonal, where t
Total synthesis of graphislactones A, C, D, and H, of ulocladol, and of the originally proposed and revised structures of graphislactones e and F
Altemoeller, Martina,Gehring, Timo,Cudaj, Judith,Podlech, Joachim,Goesmann, Helmut,Feldmann, Claus,Rothenberger, Alexander
experimental part, p. 2130 - 2140 (2009/09/29)
Graphislactones A-H and the structurally related ulocladol are highly oxygenated resorcylic lactones produced by lichens and fungi. We present total syntheses of graphislactones A, C-F, H and of ulocladol. Graphislactones E, F, and H were synthesized for the first time. The spectra of graphislactones E and F synthesized as the originally proposed structures were not in agreement with published data. Consequently, revised structures for these compounds are proposed, whose correctness is unambiguously proven by total synthesis and comparison of the spectroscopic data. Key steps in all syntheses are Suzuki couplings for the construction of the central biaryl bond and Dakin reactions to supply further hydroxy groups required in these highly oxygenated substrates. Graphislactones A, C, and H, acylated graphislac- tone D and ulocladol were prepared in 8-11 steps with 7-20% yield starting with purchasable compounds, where the longest linear sequence consists of 5-9 steps. The syntheses are thus significantly shorter than the previously published syntheses of graphislactones A-D and of ulocladol. Graphis- lactones E and F were synthesized in 8 steps, where the longest linear sequences consist of 6 and 5 steps, respectively. They were isolated as the respective acetylated compounds with 25 and 10% yield.
Total synthesis of neoaltenuene
Altemoeller, Martina,Podlech, Joachim
experimental part, p. 2275 - 2282 (2009/08/09)
The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key r
