ArticleOrganic letters2015
Total Synthesis of Oridamycins A and B.
Article in Organic letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- A chiral LC-MS strategy for stereochemical assignment of natural products sharing a 3-methylpent-4-en-2-ol moiety in their terminal structures.Beilstein journal of organic chemistry · 2025Article
- Highly chemoselective oxidative dimerization of indolosesquiterpene alkaloids: a biomimetic approach to dixiamycin.Chemical science · 2024Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Total synthesis of atropisomeric indolosesquiterpenoidsChemical science · 2023Article
- Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.Angewandte Chemie (International ed. in English) · 2020Article
- Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties.Angewandte Chemie (International ed. in English) · 2019Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.The Journal of organic chemistry · 2018Article
- Divergent Synthesis of Pyrone Diterpenes via Radical Cross Coupling.Journal of the American Chemical Society · 2018Article
- Toward a Unified Total Synthesis of the Xiamycin and Oridamycin Families of Indolosesquiterpenes.The Journal of organic chemistry · 2017Article
- Characterization of the flavoenzyme XiaK as anChemical science · 2017Article
- Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin.Journal of the American Chemical Society · 2016Article
- Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.Journal of the American Chemical Society · 2016Article
Corrections and comments
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Authors and funding
1 author.
Funding
Abstract
The total synthesis of both oridamycin A and oridamycin B was accomplished starting from a common synthetic intermediate readily prepared from geranyl acetate. The sequence utilizes an oxidative radical cyclization to construct the trans-decalin ring system, setting three of four contiguous stereocenters in one operation. The carbazole nucleus was forged through a one-pot process entailing acid-promoted dehydration followed by 6π-electrocyclization/aromatization.
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Registered trials
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