@article{9e51d800ee9c400ea1988bfae6be4ab3,
title = "Synthesis of (+)-Lineariifolianone and Related Cyclopropenone-Containing Sesquiterpenoids",
abstract = "A synthesis of the proposed structure of lineariifolianone has been achieved in eight steps and 9% overall yield starting from (+)-valencene, leading to a reassignment of the absolute configuration of this unusual cyclopropenone-containing natural product. Key steps in the synthetic route include kinetic protonation of an enolate to epimerize the C7 stereocenter and a stereoconvergent epoxide opening to establish the trans-diaxial diol functionality. The syntheses of the enantiomers of two other closely related natural products are also reported, confirming that all three compounds belong to the eremophilane class of sesquiterpenoids.",
author = "Reber, {Keith P.} and Gilbert, {Ian W.} and Strassfeld, {Daniel A.} and Sorensen, {Erik J.}",
note = "Funding Information: We gratefully acknowledge the Fisher College of Science and Mathematics (Towson University) for financially supporting this project through a Jess and Mildred Fisher Endowed Professorship in the Biological and Physical Sciences (K.P.R.). Undergraduate summer research fellowships were provided by the Camille & Henry Dreyfus Foundation (I.W.G.) and the Princeton Environmental Institute's Grand Challenges Health Initiative (D.A.S.). This material is based upon work supported by the National Science Foundation under Grant Nos 0923051 and 1531562. We also thank Dr. John Eng (Princeton University) for performing high-resolution GC?MS analyses. Funding Information: We gratefully acknowledge the Fisher College of Science and Mathematics (Towson University) for financially supporting this project through a Jess and Mildred Fisher Endowed Professorship in the Biological and Physical Sciences (K.P.R.). Undergraduate summer research fellowships were provided by the Camille & Henry Dreyfus Foundation (I.W.G.) and the Princeton Environmental Institute{\textquoteright}s Grand Challenges Health Initiative (D.A.S.). This material is based upon work supported by the National Science Foundation under Grant Nos 0923051 and 1531562. We also thank Dr. John Eng (Princeton University) for performing high-resolution GC−MS analyses. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = may,
day = "3",
doi = "10.1021/acs.joc.9b00478",
language = "English (US)",
volume = "84",
pages = "5524--5534",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "9",
}