29. Evolution of the Short Enantioselective Total Synthesis of the Unique Marine Myxobacteria Tetracyclic Polyketide Salimabromide
Gan, K.-G.#; Zhu, Y.#; Shi, G.; Wu, C.; Ni, F.-Q.; Zhao, L.-H.; Dou, X.; Zhang, Z.*; Lu, H.-H.* Chin. J. Chem. 2025, 43, 79-89; DOI: 10.1002/cjoc.202400751.
- The full story of the synthesis of salimabromide
- A new application of kinetic isotope effects in natural product synthesis.
28. Total Synthesis of (-)-Daphenylline by Gold-Catalyzed Intramolecular Dearomatization Reaction of Methoxynaphthalene
Cao, M.-Y.; Gu, Q.-X.; Long, J.; Fang, X.; Lu, H.-H.* Adv. Synth. Catal. 2024, 366, 4194-4198; DOI: 10.1002/adsc.202400699.
- Invited for a special issue of "Dearomatization"
- A new concise synthesis of (-)-daphenylline by means of a gold-catalyzed dearomatization reaction of β-methoxynaphthalene
- a new organocatalytic asymmetric Mukaiyama–Michael reaction
27. Asymmetric Hydrogenation of Tetrasubstituted β-Phosphorylated α,β-Unsaturated Esters Catalyzed by Nickel Complexes of Chiral Phosphinooxazolines
Peng, Z.; Gu, Q.-X.; Zhu, Y.; Lu, H.-H.* Cell Rep. Phys. Sci. 2024, 5, 102261; DOI: 10.1016/j.xcrp.2024.102261.
- The first asymmetric hydrogenation of tetrasubstituted olefins by chiral Ni(II)-PHOX catalysts
- A new class of chiral bisphosphine ligands was developed
26. Enantioselective Total Synthesis of (+)-Propolisbenzofuran B
Xu, W.-X.; Zhao, L.-H.; Zhu, Y.; Lu, H.-H.* Chin. J. Chem. 2024, 42, 2833-2839; DOI: 10.1002/cjoc.202400563.
- Invited for a special issue of "Emerging Investigators in 2024"
- The first catalytic asymmetric total synthesis
- Strategic use of Rh-catalyzed enantioselective hydrogenation of a tetrahydrodiebenzo[b,d]furan-type tetrasubstituted olefin and C(sp3)-H oxidations
- A powerful general platform for cyclolignan synthesis with ideal modularity and diversity
- Strategic use of Rh-catalyzed enantioselective hydrogenation of a new class of all-carbon tetrasubstituted olefins and C(sp3)-H functionalizations
- Structural revision of a number of cyclolignans
24. Taming Chiral Quaternary Stereocenters via Remote H-Bonding Stereoinduction in Palladium-Catalyzed (3+2) Cycloadditions
Xiao, Y.-Q.; Li, M.-M.; Zhou, Z.-X.; Li, Y.-J. Cao, M.-Y.; Liu, X.-P.; Lu, H.-H.; Rao, L.*; Lu, L.-Q.*; Beauchemin, A. M.; Xiao, W.-J. Angew. Chem. Int. Ed. 2022, 62, e202212444.
- A new application of our Trost-type ligands (Thanks Liang-Qiu!)
- The first palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition of vinyl cyclopropanes bearing two different electron-withdrawing groups
23. Concise Total Synthesis of Salimabromide
Lu, H.-H.*; Gan, K.-G.#; Ni, F.-Q.#; Zhang, Z.; Zhu, Y. J. Am. Chem. Soc. 2022, 144, 18778-18783; DOI: 10.1021/jacs.2c08337.
- Simutaneous construction of the unique benzo-fused [4.3.1] framework and the vicinal quaternary carboncenters via a HAT-mediated cyclization (Giese-Baran reaction)
- A novel tandem oxidative reaction was developed to form the butyrolactone and enone moieties concurrently
22. Concise Enantioselective Total Synthesis of Daphenylline Enabled by an Intramolecular Oxidative Dearomatization (Highlighted in Synfacts 2022, 18, 0586.)
Cao, M.-Y.#; Ma, B.-J.#; Gu, Q.-X.; Fu, B.; Lu, H.-H.* J. Am. Chem. Soc. 2022, 144, 5750-5755; DOI: 10.1021/jacs.2c01674.
- The first oxidative dearomatization reaction of naphthols for the synthesis of fused rings
- An unprecedented remote acid-directed Mukaiyama-Michael reaction
- A strategic tandem reductive amination/amidation double cyclization reaction
21. Nonafluorobutanesulfonyl Fluoride (Second Update)
Lu, H.-H.* Encyclopedia of Reagents for Organic Synthesis 2022; DOI: 10.1002/047084289X.rn061.pub3 (Invited).
20. Enantioselective Addition-Alkylation of α,β-Unsaturated Carbonyls via Bisguanidinium Silicate Ion Pair Catalysis
Chen, W.; Ang, E. C. X.; Tan, S. M.; Chua, Z.; Ren, J.; Yang, Z.; Teng, B.; Lee, R.*; Lu, H.-H.*; Tan, C.-H.* J. Am. Chem. Soc. 2020, 142, 19065-19070; DOI: 10.1021/jacs.0c00183.
- Vicinal carbon stereocenters constructed with excellent selectivities (up to 99% ee, >99:1 dr)
- Penta-coordinated silicates are crucial intermediates
19. Enantioselective Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation of Benzofurans: Diversity-Oriented Synthesis of Flavaglines
Lu, H.-H.*; Cao, M.-Y. Sylett (Synpacts) 2021, 1981-1986; DOI: 10.1055/a-1650-4266 (Invited).
18. Optically Active Flavaglines-Inspired Molecules by a Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation
Cao, M.-Y.; Ma, B.-J.; Lao, Z.-Q.; Wang, H.; Wang, J.; Liu, J.; Xing, K.; Huang, Y.-H.; Gan, K.-J.; Gao, W.; Wang, H.; Hong, X.; Lu, H.-H.* J. Am. Chem. Soc. 2020, 142, 12039-12045; DOI: 10.1021/jacs.0c05113.
- A new class of Trost-type ligands bearing a chiral cycloalkane framwork
- An unprecedented Pd-catalyzed dearomative AAA (> 30 examples, up to 96% ee)
- A new blueprint for flavagline-based drug development by a DOS design
17. Catalytic Asymmetric Synthesis of a New Class of CyPHOX Ligands
Cao, M.-Y.#; Xu, Z.-M.#; Gao, W.; Liu, J.; Tan, F.*; Lu, H.-H.* Tetrahedron 2019, 75, 3282-3291; DOI: 10.1016/j.tet.2019.04.050.
- Invited for Ryan Shenvi Award Issue
- Four newly designed CyPHOX ligands with chiral cyclohexane scaffold replacing the previous planar aryl group of PHOX ligands, were efficiently prepared.
- Preliminary tests with these CyPHOX ligands showed that they exhibited better performance (44-67% ee) than the privileged PHOX ligand (13% ee) in Lam's nickel-catalyzed desymmetrizing arylative cyclization
16. Witkin, J. M.*; Shenvi, R. A.; Li, X.; Gleason, S. D.; Weiss, J.; Morrow, D.; Catow, J. T.; Wakulchik, M.; Ohtawa, M.; Lu, H.-H.; Martinez, M. D.; Schkeryantz, J. M.; Carpenter, T. S.; Lightstone, F. C.; Cerne, R. Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies, Biochem. Pharm. 2018, 155, 61-70.
15. Lu, H.-H.#; Pronin, S.#; Antonova-Koch, Y.; Meister, S.; Winzeler, E. A.; Shenvi, R. A.* Synthesis of (+)-7,20-Diisocyanoadociane and Liver Stage Antiplas-modial Activity of the ICT Class, J. Am. Chem. Soc. 2016, 138, 7268-7271.
14. Lu, H.-H.; Martinez, M. D.; Shenvi, R. A.* An Eight-step, Gram-Scale Synthesis of (–)-Jiadifenolide, Nat. Chem. 2015, 7, 604-607.
- Highlighted in Chemistry World, July 27 2015;
- Highlighted by E. M. Carreira and M. Westph, Synfacts 2015, 11, 089;
- #1 most read article, June-July 2015.
13. Lu, H.-H.; Hinkelmann, B.; Tautz, T.; Li, J.; Franke, R.; Sasse, F.; Kalesse, M.* Paleo-Soraphens: Chemical Total Syntheses and Biological Studies, Org. Biomol. Chem. 2015, 13, 8029-8036.
12. Kalesse, M.*; Cordes, M.; Symkenberg, G.; Lu, H.-H. The Vinylogous Mukaiyama Aldol Reaction (VMAR) in Natural Product Synthesis, Nat. Prod. Rep. 2014, 31, 563-594.
11. Lu, H.-H.; Raja, A.; Franke, R.; Landsberg, D.; Sasse, F.; Kalesse, M.* Syntheses and Biological Evaluation of Paleo-Soraphens, Angew. Chem. Int. Ed. 2013, 52, 13549-13552.
10. Duan, S.-W.; Lu, H.-H.; Zhang, F.-G.; Xuan, J.; Chen, J.-R.; Xiao, W.-J.* Organocatalytic Conjugate Additions of Acetylacetone to 3-Ylideneoxindoles: A Direct Access to Highly Enantioenriched Oxindole Derivatives, Synthesis 2011, 1847-1852.
9. Lu, H.-H.; Tan, F.; Xiao, W.-J.* Enantioselective Organocatalytic Friedel-Crafts Alkylations, Curr. Org. Chem. 2011, 15, 4022-4045. (Invited Review)
8. Zhang, F.-G.; Yang, Q.-Q.; Xuan, J.; Lu, H.-H.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J.* Enantioselective Conjugate Addition of Oximes to Trisubstituted β-Nitroacrylates: An Organocatalytic Approach to β2,2-Amino Acid Derivatives, Org. Lett. 2010, 12, 5636–5639.
7. Lu, H.-H.; Liu, H.; Wu, W.; Wang, X.-F.; Lu, L.-Q.; Xiao, W.-J.* Catalytic Asymmetric Intramolecular Hydroarylations of ω-Aryloxy- and Arylamino Tethered α,β-Unsaturated Aldehydes, Chem. Eur. J. 2009, 15, 2742-2746.
6. Lu, H.-H.; Meng, X.-G.; Zhang, F.-G.; Duan, S.-W.; Xiao, W.-J.* Enantioselective Michael Reactions of β,β-Disubstituted Nitroalkenes: A New Approach to β2,2-Amino Acids with Hetero-Quaternary Stereocenters, Org. Lett. 2009, 11, 3946-3949.
5. Lu, H.-H.; Wang, X.-F.; Yao, C.-J.; Zhang, J.-M.; Wu, H.; Xiao, W.-J.* Highly Enantioselective Organocatalytic Michael Addition of Nitroalkanes to 4-oxo-Enoates, Chem. Commun. 2009, 4251-4253.
4. Chen, J.-R.; Lai, Y.-Y.; Lu, H.-H.; Wang, X.-F.; Xiao, W.-J.* Highly Enantioselective Desymmetrization of meso- and Prochiral Cyclic Ketones via Organocatalytic Michael Reaction, Tetrahedron 2009, 65, 9238-9243.
3. Dong, H.-M.; Lu, H.-H.; Lu, L.-Q.; Chen, C.-B.; Xiao, W.-J.* Asymmetric Friedel-Crafts Alkylations of Indoles with Ethyl Glyoxylate Catalyzed by (S)-BINOL-Ti (IV) Complex: Direct Access to Enantiomerically Enriched 3-Indolyl-hydroxyacetates, Adv. Synth. Catal. 2007, 349, 1597-1603.
2. Cao, Y.-J.; Lu, H.-H.; Lai, Y.-Y.; Lu, L.-Q.; Xiao, W.-J.* An Effective Bifunctional Thiourea Catalyst for Highly Enantio- and Diastereoselective Michael Addition of Cyclohexanone to Nitroolefins, Synthesis 2006, 3795-3800.
1. Chen, J.-R.; Lu, H.-H.; Li, X.-Y.; Cheng, L.; Wan, J.; Xiao, W.-J.* Readily Tunable and Bifunctional L-Prolinamide Derivatives: Design and Application in the Direct Enantioselective Aldol Reactions, Org. Lett. 2005, 7, 4543-4545.
#These authors contributed equally.
