Journal of the Chemical Society. Perkin transactions I p. 2619 - 2622 (1996)
Update date:2022-08-05
Topics:
Bracher, Franz
Schulte, Brigitte
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.
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