ArticleNature2016
Nineteen-step total synthesis of (+)-phorbol.
Article in Nature, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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Who cites it
60 citing papers in PubMed, 241 citations in OpenAlex.
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- Evolution of a Synthetic Strategy for Complex Diterpenes fromJournal of the American Chemical Society · 2026Article
- Spatial Control Over Tether-Tunable Coordination on Palladium for Divergent Synthesis of Bicyclo[n.1.0]alkanes via Oxidative Cyclopropanation of Enynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Total synthesis of natural products based on hydrogenation of aromatic rings.Beilstein journal of organic chemistry · 2026Review
- Divergent synthesis of Haplomitrium diterpenoids via a late-stage biomimetic skeletal reorganization approach.Nature communications · 2025Article
- Total Synthesis of (-)-Neocucurbol C Enabled by Pattern Recognition and MHAT Cyclization.Journal of the American Chemical Society · 2025Article
- Synthesis of diverse terpenoid frameworks via enzyme-enabled abiotic scaffold hop.Nature chemistry · 2025Article
- Trimerization of 1,2-Diaminocyclohexane Catalyzed by a Metal-Organic Cage Tandem Catalyst with Dual Biomimetic Active Sites.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Molecular complexity as a driving force for the advancement of organic synthesis.Nature reviews. Chemistry · 2024Review
- Asymmetric total synthesis of polycyclic xanthenes and discovery of a WalK activator active against MRSA.Nature communications · 2024Article
- Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide.Nature communications · 2024Article
- Medium-Sized Ring Expansion Strategies: Enhancing Small-Molecule Library Development.Molecules (Basel, Switzerland) · 2024Review
- Synthesis of nimbolide and its analogues and their application as poly(ADP-ribose) polymerase-1 trapping inducers.Nature synthesis · 2024Article
- Article
- Tigliane Diterpenoids.Progress in the chemistry of organic natural products · 2024Review
- Total Synthesis of (+)-Euphorikanin A via an Atropospecific Cascade.Journal of the American Chemical Society · 2023Article
- EngineeringmLife · 2023Article
- Radical and Cationic Pathways in C(Journal of the American Chemical Society · 2023Article
- Catalytic 4-exo-dig carbocyclization for the construction of furan-fused cyclobutanones and synthetic applications.Nature communications · 2023Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
Abstract
Phorbol, the flagship member of the tigliane diterpene family, has been known for over 80 years and has attracted attention from many chemists and biologists owing to its intriguing chemical structure and the medicinal potential of phorbol esters. Access to useful quantities of phorbol and related analogues has relied on isolation from natural sources and semisynthesis. Despite efforts spanning 40 years, chemical synthesis has been unable to compete with these strategies, owing to its complexity and unusual placement of oxygen atoms. Purely synthetic enantiopure phorbol has remained elusive, and biological synthesis has not led to even the simplest members of this terpene family. Recently, the chemical syntheses of eudesmanes, germacrenes, taxanes and ingenanes have all benefited from a strategy inspired by the logic of two-phase terpene biosynthesis in which powerful C-C bond constructions and C-H bond oxidations go hand in hand. Here we implement a two-phase terpene synthesis strategy to achieve enantiospecific total synthesis of (+)-phorbol in only 19 steps from the abundant monoterpene (+)-3-carene. The purpose of this synthesis route is not to displace isolation or semisynthesis as a means of generating the natural product per se, but rather to enable access to analogues containing unique placements of oxygen atoms that are otherwise inaccessible.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.