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Short and Efficient Synthesis of Cadiolide B
The first synthesis of cadiolide B has been achieved in 6 steps and 42% overall yield from 4-bromo-2(5H)-furanone. The pathway involves sequential, regiocontrolled introduction of the three furanone…
Concise Synthesis of Yingzhaosu C and epi-Yingzhaosu C by Peroxyl Radical Cyclization. Assignment of Relative Configuration.
Synthesis of the Marine Myxobacterial Antibiotic Enhygrolide A.
- Ramesh Muddala, J. M. Acosta, L. Barbosa, J. Boukouvalas
- Biology, MedicineJournal of natural products
- 21 June 2017
The first synthesis of enhygrolide A, a scarce γ-alkylidenebutenolide antibiotic of the obligate marine myxobacterium Enhygromyxa salina, was achieved in five steps and 54% overall yield from…
Reaction of singlet oxygen with enol ethers in the presence of acetaldehyde. Formation of 1,2,4-trioxanes
Direct Observation of Molecular Preorganization for Chirality Transfer on a Catalyst Surface
It is shown that the investigation of heterogeneous asymmetric induction with single-site resolution sufficient to distinguish stereochemical conformations at the submolecular level is finally accessible and that the chiral modifier induces prochiral switching on the surface.
Total Synthesis of (+)-Dysidiolide
Dysidiolide (1 or ent-1), a novel sesterterpenoid isolated in 1996 from the Caribbean sponge Dysidea etheria de Laubenfels, exhibits antitumor activity at the micromolar level, and most importantly,…
General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid.
- J. Boukouvalas, Richard P. Loach
- Chemistry, MedicineThe Journal of organic chemistry
- 18 September 2008
A variety of alpha-substituted butenolides were efficiently prepared from 3- bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles to produce an anti-inflammatory marine natural product.
Benzyloxycarbonylphenylalanylcitrulline p-nitroanilide as a substrate for papain and other plant cysteine proteinases.
- C. J. Gray, J. Boukouvalas, R. J. Szawelski, C. Wharton
- Biology, MedicineThe Biochemical journal
- 1 April 1984
It is concluded that benzyloxycarbonylphenylalanylcitrulline p-nitroanilide is a highly selective substrate for the sensitive detection and assay of the plant cysteine proteinases.
Asymmetric total synthesis of (-)-panacene and correction of its relative configuration.
- J. Boukouvalas, Martin Pouliot, J. Robichaud, S. MacNeil, V. Snieckus
- Chemistry, MedicineOrganic letters
- 6 July 2006
The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core.
Noncovalent Immobilization of Optimized Bacterial Cytochrome P450 BM3 on Functionalized Magnetic Nanoparticles
- A. Bahrami, T. Vincent, A. Garnier, F. Larachi, J. Boukouvalas, M. Iliuta
- 25 September 2017
A stable insoluble P450 BM3 system that can be easily separated from the reaction medium for recycling, while using less-expensive cofactors (NADH and BNAH) than costly NADPH, can represent a…