TY - JOUR
T1 - Total synthesis of the proposed structure of trichodermatide A
AU - Myers, Eddie
AU - Herrero-Gómez, Elena
AU - Albrecht, Irina
AU - Lachs, Jennifer
AU - Mayer, Peter
AU - Hanni, Matti
AU - Ochsenfeld, Christian
AU - Trauner, Dirk
N1 - Publisher Copyright:
© 2014 American Chemical Society.
PY - 2014/10/17
Y1 - 2014/10/17
N2 - A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed 13C shifts agree well with the present NMR measurements. (Chemical Equation Presented).
AB - A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed 13C shifts agree well with the present NMR measurements. (Chemical Equation Presented).
UR - http://www.scopus.com/inward/record.url?scp=84908241359&partnerID=8YFLogxK
U2 - 10.1021/jo501206k
DO - 10.1021/jo501206k
M3 - Article
SN - 0022-3263
VL - 79
SP - 9812
EP - 9817
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 20
ER -