10.1021/jo400083v.s001 Kavirayani R. Prasad Kavirayani R. Prasad Phaneendra Gutala Phaneendra Gutala Total Synthesis and Determination of the Absolute Configuration of 5,6-Dihydro-α-pyrone Natural Product Synargentolide B American Chemical Society 2013 stereochemistry synthesis chiral phosphonate Total Synthesis Absolute Configuration product synargentolide B 2013-04-05 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Total_Synthesis_and_Determination_of_the_Absolute_Configuration_of_5_6_Dihydro_pyrone_Natural_Product_Synargentolide_B/2426806 Enantiospecific total synthesis and determination of the absolute stereochemistry of the α-pyrone-containing natural product synargentolide B were accomplished. The absolute stereochemistry of the natural product was established by synthesizing the possible diastereomers and comparison of the data with those reported for the natural product. During the process, total synthesis of the putative structure of related natural product 6<i>R</i>-[1<i>S</i>,2<i>R</i>,5<i>R</i>,6<i>S</i>-(tetraacetyloxy)-3<i>E</i>-heptenyl]-5,6-dihydro-2<i>H</i>-pyran-2-one was also accomplished and confirmed by X-ray crystal structure analysis. Wittig–Horner reaction of a chiral phosphonate derived from (<i>S</i>)-lactic acid and ring-closing metathesis were the key reactions during the course of the total synthesis.