- Successive Nucleophilic and Electrophilic Allylation for the Catalytic Enantioselective Synthesis of 2,4-Disubstituted Pyrrolidines
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Successive nucleophilic and electrophilic allylation mediated by the bis-Boc-carbonate derived from 2-methylene-1,3-propane diol enables formation of enantiomerically enriched 2,4-disubstituted pyrrolidines. An initial enantioselective iridium-catalyzed t
- Luo, Guoshun,Xiang, Ming,Krische, Michael J.
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- An efficient large-scale synthesis of EDP-420, a first-in-class bridged bicyclic macrolide (BBM) antibiotic drug candidate
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A multistep, practical, and cost-effective synthesis of novel bridged bicyclic macrolide drug candidate EDP-420 (1) is described. Starting from inexpensive and commercially available erythromycin A 9-oxime, the current chemical process involves a series of transformations: triacetylation, Pd-catalyzed O,O-bis-allylation (bridge formation), acid-catalyzed sugar cleavage, oxime reduction, acetylation, Os-catalyzed bridge olefin oxidative cleavage, Corey-Kim oxidation, bridge oxime formation, deprotection, and final purification. Multikilogram quantities have been synthesized.
- Xu, Guoyou,Tang, Datong,Gai, Yonghua,Wang, Guoqiang,Kim, Heejin,Chen, Zhigang,Phan, Ly T.,Or, Yat Sun,Wang, Zhe
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- Assembly of Terpenoid Cores by a Simple, Tunable Strategy
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Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
- Lahtigui, Ouidad,Emmetiere, Fabien,Zhang, Wei,Jirmo, Liban,Toledo-Roy, Samira,Hershberger, John C.,Macho, Jocelyn M.,Grenning, Alexander J.
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supporting information
p. 15792 - 15796
(2016/12/16)
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- Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
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Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
- Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
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supporting information
p. 11799 - 11804
(2014/10/16)
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- 6,11-3c-bicyclic 8a-azalide derivatives
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Compounds of Formula (I), and pharmaceutically acceptable salts, esters, and prodrugs thereof: (I) are disclosed, wherein A, B, D, L, X, Y, Z and R2′, are described herein. The compounds exhibit antibacterial properties. The compounds of Formul
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Page/Page column 30
(2009/06/27)
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- Processes for the preparation of 0-(2-aminobenzo[d]oxazol-5-yl)methyl hydroxylamine for the synthesis of 6,11-bicyclic erythromycin derivative EDP-182
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The present invention relates to processes and intermediates for the preparation of 6-11 bicyclic erythromycin derivative known as EDP-182 (IX-a). In particular, the present invention relates to processes and intermediates for the preparation of O-(2-amin
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Page/Page column 17
(2008/06/13)
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- 8A,11-BICYCLIC 8A-AZALIDE DERIVATIVES
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The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforemen
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Page/Page column 22
(2010/11/29)
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- TETRACYLIC BICYCLOLIDES
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The present invention discloses compounds of formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: (I) which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
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Page/Page column 74
(2008/06/13)
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- Spirocyclic bicyclolides
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The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforemen
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Page/Page column 18
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF T-11 BICYCLIC ERYTHROMYCIN DERIVATIVES
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The present invention relates to processes and intermediates for the preparation of 6-11 bicyclic erythromycin derivatives. In particular, the presen tinvention relates to processes and intermediates for the preparation of a compound of formula (IX-c).
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Page/Page column 33
(2010/02/13)
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- 9a, 11-3C-BICYCLIC 9a-AZALIDE DERIVATIVES
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The present invention discloses compounds of formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof, which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
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Page/Page column 56
(2008/06/13)
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- 6-11 BICYCLIC KETOLIDE DERIVATIVES
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The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: (I) which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the afor
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Page/Page column 98
(2010/02/12)
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- 6-11 BICYCLIC KETOLIDE DRIVATIVES
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The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: Formule (I) which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising
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Page/Page column 104
(2010/02/12)
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- BRIDGED MACROCYCLIC COMPOUNDS AND PROCESSES FOR THE PREPARATION THEREOF
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The present invention provides a method for preparing bridged macrocyclic compounds comprising the step of reacting a macrocyclic compound characterized by having at least two nucleophilic moieties with a bifunctional bridging reagent optionally in the presence of a catalyst, thereby producing a bridged macrocyclic product.
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Page/Page column 30
(2010/02/13)
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- Processes for the preparation of 6-11 bicyclic erythromycin derivatives
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The present invention relates to processes and intermediates for the preparation of 6-11 bicyclic erythromycin derivatives. In particular, the present invention relates to processes and intermediates for the preparation of a compound of formula (IX-c):
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- Synthesis of novel 6,11-o-bridged bicyclic ketolides via a palladium-catalyzed bis-allylation
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(Chemical equation presented) A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-π-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.
- Wang, Guoqiang,Niu, Deqiang,Qiu, Yao-Ling,Phan, Ly Tam,Chen, Zhigang,Polemeropoulos, Alexander,Or, Yat Sun
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p. 4455 - 4458
(2007/10/03)
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- 6-11 BICYCLIC KETOLIDE DERIVATIVES
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The present invention discloses compounds of formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforem
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Page/Page column 104
(2010/02/07)
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