Conversion of Phorbol into Des-D-Ring Tricycle and Crotonianoid B via Peroxidation Reaction
Ayumu Watanabe,
Yuto Hikone,
Masanori Nagatomo
et al.
Abstract:Phorbol (1) has a tetracyclic
ABCD-ring and is readily
isolable from a natural source. We previously synthesized 1 and 16 structurally related natural products using common ABC-ring
intermediate 2. Here we report a new synthetic route
to 2 using 1 as a starting material. Key
features of the synthesis are chemoselective removal of the D-ring
via cyclopropane opening, peroxidation, and retro-aldol reactions.
The high utility of the peroxidation was further demonstrated in the
first synthesis of crotonianoid B (9… Show more
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