Total synthesis of erythromycins. 4. Total synthesis of erythronolide B

Corey, E. J.; Kim, Sunggak; Yoo, Sung Eun; Nicolaou, K. C.; Melvin, Lawrence S.; Brunelle, Daniel J.; Falck, John R.; Trybulski, Eugene J.; Lett, Robert; Sheldrake, Peter

doi:10.1021/ja00482a063

Cited by 152 publications

(28 citation statements)

References 4 publications

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“…Corey at Harvard University, and was involved in the synthesis of a macrocyclic lactone, Erythronolide B. 17 My work had mainly been involved with designing reagents and procedures for ring-closure of the 14-membered lactone ring from an x-hydroxy carboxylic acid. The technique we ultimately used involved formation of an active ester (a thioimidazole species), followed by slow dropwise addition to a heated solution, which would afford ring-closure to the lactone.…”

Section: Initial Cyclization Strategiesmentioning

confidence: 99%

Cyclic oligomer chemistry

Brunelle

2008

J. Polym. Sci. A Polym. Chem.

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Cyclic oligomers of engineering plastics such as polycarbonate and aromatic polyesters have been known for some time, being formed at very low levels during commercial manufacture. At GE Global Research, we have devised methods for high-yielding and selective preparation of such cyclic oligomers, that are amenable to commercial manufacture. The mixtures of cyclic oligomers have melting points significantly lower than individual ring sizes, and have very low viscosities in the melt. Ring-opening polymerization using appropriate initiators affords rapid reactions (2-6 min) without measurable exotherm, providing very high-molecularweight polymers and without reaction byproducts. These materials have been scaled to commercial quantities, and have shown to be extremely useful for fabrication of glass and carbon fiber composites with high-fiber fractions.

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Section: Initial Cyclization Strategiesmentioning

confidence: 99%

Cyclic oligomer chemistry

Brunelle

2008

J. Polym. Sci. A Polym. Chem.

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“…ErythronolideB was obtained from 15 by a simple reaction sequence. [20] The double-activation method has been used effectively for the synthesis of a number of other remarkable natural macrocyclic lactones (Scheme 5) including brefeldin A (16), an inhibitor of protein transport and processing in mammalian the microbial iron transporter enterobactin (17), ["] …”

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confidence: 99%

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

Corey

1991

Angew. Chem. Int. Ed. Engl.

367

206

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“Chemical synthesis is uniquely positioned at the heart of chemistry, and its impact on our lives and society is all‐pervasive.” Elias James Corey expresses this opinion in his Nobel Lecture, in which he discusses the origin and development of his contributions leading to the award of the Nobel Prize in chemistry in 1990. His concept of retrosynthetic analysis revolutionized both the practice and teaching of organic chemistry. His application of computers to synthetic planning was pioneering. The numerous synthetic methods developed by him and his co‐workers have proven invaluable in organic synthesis. Finally, the total syntheses carried out in his laboratories—for example, the synthesis of gibberellic acid and of ginkgolide B—are milestones in the breathtaking development of organic synthesis over the last thirty years.

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“…J. Corey et al published in 1978 the first total synthesis of (¡)-erythronolide B (Scheme 23). 33 The creation of the syn, syn, syn stereotetrad began from the achiral dienone 176 by hydroboration followed by oxidation, to produce the dienone acid 177. Treatment with bromine-potassium bromide solution yielded the bromo lactone 178, which was then converted under basic reaction conditions to the epoxy acid 179.…”

Section: Syn Syn Syn: Erythromycin A/b and Erythronolide A/bmentioning

confidence: 99%

Polyketide stereotetrads in natural products

Koskinen¹,

Karisalmi²

2005

Chem. Soc. Rev.

127

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Natural products (or secondary metabolites) remain as the most important source for discovery of new and potential drug molecules. With high resolution data of their structures, and the advancement of synthesis possibilities, analysis of the natural products based on their specific structural features is valuable to those entering the field. In this tutorial review we attempt such an analysis indicating the salient features of the structural classes with examples of the synthesis of each one of them. As the particular class of natural products, we have chosen polyketides.

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Total synthesis of erythromycins. 4. Total synthesis of erythronolide B

Cited by 152 publications

References 4 publications

Cyclic oligomer chemistry

Cyclic oligomer chemistry

The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)

Polyketide stereotetrads in natural products

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