Total synthesis and absolute stereochemistry of plakortone D.
The first total synthesis of plakortone D is described and thereby establishes the structure and absolute stereochemistry of the most biologically active member of the marine-derived plakortone family. The sterically congested bicyclic lactone core results from a Pd(II)-induced hydroxycyclization-carbonylation-lactonization sequence on an enediol whose chirality was installed by AD-technology. Attachment of the side chain, also constructed using AD-methodology, was achieved by using a modified Julia coupling. The described approach enables acquisition of other plakortones and analogues, in the correct (natural) stereochemical series.
Hayes
Patricia Y
PY
Department of Chemistry, The University of Queensland, Brisbane 4072, Australia.
Kitching
William
W
D000818:Animals; D007783:Lactones / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
D007783:Lactones; C466488:plakortone D