@article{a48b3614d8b249a4be2ca3158e10f3b0,
title = "Synthesis of pinnaic acid; asymmetric construction of spirocyclic core",
abstract = "An asymmetric synthesis of the spirocyclic core of pinnaic acid, a cPLA2 inhibitor, is described. A key transformation in the sequence involves an asymmetric Michael-initiated ring closure.",
keywords = "Alkaloids, Asymmetric synthesis, Marine metabolites, Spiro compounds",
author = "Hirokazu Arimoto and Shigehiro Asano and Daisuke Uemura",
note = "Funding Information: Alkylation of ester enolate of 10 with prenyl bromide occured with complete facial selctivity from the side as expected, due to the shielding of a-side chain at C 13. This was supported by the observance of n.O.e as shown in Scheme 2. Hydrolysis of the resultant methyl ester (11) required harsh conditions(KOH, DMSO, 120~C) due to steric hinderance, which also limited the use of conventional alcohol protective groups to p-methoxyphenyl ether. Treatment of carboxylic acid 12 under Curtius rearrangement conditions(diphenylphosphoryl azide, Et~N, benzene, reflux) provided isocyanate 13, which was fairly stable to",
year = "1999",
month = apr,
day = "30",
doi = "10.1016/S0040-4039(99)00578-X",
language = "English",
volume = "40",
pages = "3583--3586",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd.",
number = "18",
}