title: Synthetic approach to wortmannilactone C.
abstract: A diastereomer of wortmannilactone C has been synthesized according to a convergent and versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate. The key steps are a Liebeskind cross-coupling and a Horner-Wadsworth-Emmons (HWE) reaction to construct the macrolactone. The stereogenic centers at C9, C11, and C21 were controlled by enantioselective allyltitanations, and the C19 stereocenter was controlled by using a Noyori reduction of an acetylenic ketone.
authors: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231, ESPCI ParisTech/CNRS/PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors: Damien
authors: D
authors: Brandt
authors: Aurélia
authors: A
authors: Dittoo
authors: Véronique
authors: V
authors: Bellosta
authors: Janine
authors: J
authors: Cossy
mesh_terms: D007783:Lactones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018942:Macrolides; C000600938:wortmannilactone C