β‐Haloacetals and Ketals: 2‐(2‐Bromoethyl)‐1,3‐dioxane and 2,5,5‐Trimethyl‐2‐(2‐bromoethyl)‐1,3‐dioxane

Stowell, John C.; Keith, D. R.; King, B. T.

doi:10.1002/0471264180.os062.18

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2006

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“…The required 3-azidopropanal (5) and 3-chloropropanal (6) were prepared by addition of the corresponding acids to acrolein, with the addition of HCl being titrated using dicinnamylacetone as indicator [10]. As an efficient synthesis and isolation of 3-fluoropropanal (4) had not been previously reported, a simple process suitable for the production of this unstable synthon in a form useable in the titanium-mediated aldol without purification was developed.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Erythromycin Analogs Having Functional Groups at C-15

et al. 2006

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Chemobiosynthesis has been used to prepare analogs of erythromycins having unique functional groups at the 15-position. Using diketide thioester feeding to genetically engineered Streptomyces coelicolor, analogs of 6-deoxyerythronolide B were prepared having 15-fluoro, 15-chloro, and 15-azido groups. Bioconversion using a genetically engineered mutant of Saccharopolyspora erythraea was used to produce 15-fluoroerythromycin A and 15-azidoerythromycin A. These new erythromycin analogs provide antibacterial macrolides with unique physicochemical properties and functional groups that allow for selective derivatization.

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Section: Resultsmentioning

confidence: 99%