Concise synthesis of (25S)-Δ4-dafachronic acid and desulfated boophiline enabled by photoinduced decarboxylative allylation and asymmetric hydrogenation†
Zhaoguo
Zhang 
*a
and
Jingjing
Wu
*ab
*a
and
Jingjing
Wu
*ab
Abstract
(25S)-Δ4-Dafachronic acid and boophiline exhibit intriguing bioactivities. However, the C-25 configuration of boophiline remains undetermined. Here, we present their concise synthesis from readily available bile acids. The synthesis featured a photoinduced decarboxylative allylation followed by an asymmetric hydrogenation. A stereodivergent synthesis of both C-25 diastereomers of desulfated boophiline enabled further confirmation of its absolute configuration. Furthermore, the decarboxylative allylation was applied to the late-stage functionalization of a range of complex natural products and pharmaceuticals.
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