185038-86-2Relevant academic research and scientific papers
Total synthesis of virgatolide b via exploitation of intramolecular hydrogen bonding
Hume, Paul A.,Furkert, Daniel. P.,Brimble, Margaret A.
, p. 5269 - 5281 (2014/06/23)
A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp3-sp2 Suzuki-Miyaura cross-coupling of a β-trifluoroboratoamide with an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction. Intramolecular hydrogen bonding governed the regioselectivity of the key spiroketalization step, affording the natural product as a single regioisomer.
Enantiodivergent synthesis of both enantiomers of the macrocyclic lactone lasiodiplodin
Bracher, Franz,Schulte, Brigitte
, p. 2619 - 2622 (2007/10/03)
A straightforward approach to both enantiomers of lasiodiplodin 1 is described utilizing (S)-2-(2-hydroxypropyl)-1,3-dithiane 3 as a chiral building block. The key step is a Pd0-catalysed cross coupling of an arene trifluoromethanesulfonate with a 9-alkyl-9-borabicyclo[3.3.1]nonane derivative. The two enantiomers 1 and ent-1 have been obtained in an enantiodivergent manner by macrolactonization of the hydroxy acid 10 with either Gerlach's modification of the Corey lactonization or a Mitsunobu lactonization.
