A convenient synthesis of 4-and 5-acetyltropolone.

H Yamamoto, A Hara, A Noguchi, H Kawamoto…

Index: Yamamoto, Hiroshi; Hara, Atsushi; Noguchi, Ayashi; Kawamoto, Heizan; Inokawa, Saburo; Nozoe, Tetsuo Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 5 p. 1594 - 1598

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Citation Number: 6

Abstract

4-Acetyltropolone is derived from hinokitiol (β-thujaplicin) in four steps, with an overall yield of 60%, via readily available 8-azidohinokitiol. γ-Thujaplicin almost quantitatively forms its difluoroboron complex, which, upon bromination, provides an 85% yield of the 8-bromo-γ- thujaplicin difluoroboron complex. This bromo compound readily gives γ-dolabrin (87% with triethylamine) and 8-azido-γ-thujaplicin (88% with sodium azide), from which 5- ...