620161-75-3Relevant articles and documents
Successive Nucleophilic and Electrophilic Allylation for the Catalytic Enantioselective Synthesis of 2,4-Disubstituted Pyrrolidines
Luo, Guoshun,Xiang, Ming,Krische, Michael J.
, p. 2493 - 2497 (2019)
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
An efficient large-scale synthesis of EDP-420, a first-in-class bridged bicyclic macrolide (BBM) antibiotic drug candidate
Xu, Guoyou,Tang, Datong,Gai, Yonghua,Wang, Guoqiang,Kim, Heejin,Chen, Zhigang,Phan, Ly T.,Or, Yat Sun,Wang, Zhe
, p. 504 - 510 (2010)
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.
Assembly of Terpenoid Cores by a Simple, Tunable Strategy
Lahtigui, Ouidad,Emmetiere, Fabien,Zhang, Wei,Jirmo, Liban,Toledo-Roy, Samira,Hershberger, John C.,Macho, Jocelyn M.,Grenning, Alexander J.
supporting information, p. 15792 - 15796 (2016/12/16)
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.
Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
supporting information, p. 11799 - 11804 (2014/10/16)
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).
6,11-3c-bicyclic 8a-azalide derivatives
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Page/Page column 30, (2009/06/27)
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
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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Page/Page column 17, (2008/06/13)
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
8A,11-BICYCLIC 8A-AZALIDE DERIVATIVES
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Page/Page column 22, (2010/11/29)
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
TETRACYLIC BICYCLOLIDES
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Page/Page column 74, (2008/06/13)
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.
Spirocyclic bicyclolides
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Page/Page column 18, (2008/06/13)
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
PROCESS FOR THE PREPARATION OF T-11 BICYCLIC ERYTHROMYCIN DERIVATIVES
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Page/Page column 33, (2010/02/13)
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).