Tetrahedron

Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane

…, T Kasahara, K Akiyama, T Amemiya, T Kunishima…

Index: Kuroda, Chiaki; Kasahara, Takahiro; Akiyama, Kouki; Amemiya, Takuma; Kunishima, Takashi; Kimura, Yoshihiro Tetrahedron, 2002 , vol. 58, # 22 p. 4493 - 4504

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Citation Number: 14

Abstract

A new spiro-β-methylene-γ-lactone annulation reaction is addressed for the synthesis of 4- methylene-2-oxaspiro [4.5] decan-1-one and its derivatives. 2-Cyclohexylidene-3- trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl) cyclohexyl] prop-2-en-1-yl pivalate and its-1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by ...