Stereoselective Reactions. VIII. Stereochemical Requirement for the Benzylic Oxidation of Lignan Lactone. A Highly Selective Synthesis of the Antitumor Lignan Lactone Steganacin by the Oxidation of Stegane

A highly efficient synthesis of the antitumor steganin lignan steganacin (1) was accomplished. Bromination of stegane (7) with N-bromosuccinimide followed by treatment with aqueous tetrahydrofuran afforded steganol (3) in 85% yield. Acetylation of 3 gave 1 in 72% yield. Stegane (7) was also oxidized...

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