The Synthesis of Hyptol and Its C-15 Epimer from (+)-Dehydroabietic Acid

DOI: 10.1246/bcsj.64.2762

Source and publish data:

Bulletin of the Chemical Society of Japan p. 2762 - 2765 (1991)

Update date:2022-08-16

Topics:

Authors:

Matsumoto, Takashi

Terao, Hiromitsu

Wada, Makoto

Imai, Sachihiko

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Article abstract of DOI:10.1246/bcsj.64.2762

In order to elucidate the absolute configuration of C-15 in natural hyptol, methyl (15S)-13,16-dihydroxy-8,11,13-abietatrien-18-oate and its (15R)-epimer were transformed into (15S)-12,16-epoxy-11,14-dihydroxy-8,11,13-abietatrien-7-one (1a) and its (15R)-epimer (1b), respectively.The synthetic 1a was identical to natural hyptol.Thus, the stereochemistry of C-15 in the natural compound was conclusively assigned as S-configuration.

Full text of DOI:10.1246/bcsj.64.2762

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