ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Synthesis of (-)-Dihydroraputindole D by Enantioselective Benzoylation of a 1,3-Diol Intermediate.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis.Beilstein journal of organic chemistry · 2025Review
- Synthesis of (-)-Dihydroraputindole D by Enantioselective Benzoylation of a 1,3-Diol Intermediate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Abstract
The enantioselective synthesis of (-)-dihydroraputindole D is reported. The key step is the desymmetrizing benzoylation of a prochiral 1,3-diol employing Trost's ProPhenol catalyst system, which has been applied for the first time to a cyclic molecule carrying geminal hydroxymethyl groups. The cyclopenta[f]indoline system was assembled by Au(I)-catalyzed cyclization of an alkynylated indoline precursor. (-)-Dihydroraputindole D was obtained in 17 steps and 8% overall yield starting from dihydroxyacetone. In combination with quantum chemical calculations of the ECD spectra, our synthesis allowed us to determine the absolute configuration (5S,7R) of the natural product (+)-raputindole D from the Rutaceous plant Raputia simulans.
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