@article{7a059770a94b40e292a32733e6aa1e5e,
title = "Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate",
abstract = "An enantioconvergent route for natural form of ethyl shikimate was achieved from Diels-Alder adduct of furan and acryloyl chloride. The key step was a highly enantioselective (E >500) and efficient acetylation of ethyl (3R*,4S*,5S*)-5-hydroxy-3,4-isopropylidenedioxycyclohex-1- enecarboxylate, which had a diastereomeric relationship with ethyl shikimate, mediated by Burkholderia cepacia lipase (Amano PS-IM). Both of the resolved enantiomers were converted to natural form of ethyl shikimate by inversion at C-5 for the former and at C-3 and C-4 for the latter, respectively.",
keywords = "Carbacycle, Enantioconvergent approach, Ethyl shikimate, Kinetic resolution, Lipase",
author = "Yasunobu Yamashita and Kengo Hanaya and Takeshi Sugai and Tohru Mizushima and Mitsuru Shoji",
note = "Funding Information: This work was supported by MEXT-Supported Program for the Strategic Research Foundation at Private Universities, 2011–2015. We acknowledge the generous gift of lipases, from Amano Enzyme Inc. for PS-IM, Novozymes Japan for Novozym 435, and Meito Sangyo Co. Ltd. for Meito OF. ",
year = "2013",
month = aug,
day = "5",
doi = "10.1016/j.tet.2013.05.004",
language = "English",
volume = "69",
pages = "6527--6532",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "31",
}