Enantioselective synthesis of (−)-γ-jasmolactone

Missio, Lauri J.; Comasseto, J. V.

doi:10.1016/s0957-4166(00)00444-4

Cited by 16 publications

(16 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…14 No Brasil, o uso da biocatálise na síntese de compostos quirais foi uma das subáreas da catálise assimétrica que primeiro se estabeleceu, 15 e hoje conta com diversos grupos de pesquisa consolidados ou em consolidação, baseados na Unicamp, 15 UFSC, 16 na USP-São Carlos, 17 na UFRJ; 18 na UFC [19][20][21] e no IQ-USP. [22][23][24] Dentre outros estudos envolvendo enzimas isoladas 23 ou micro-organismos, 24 com a síntese de diversas classes de moléculas quirais, foi desenvolvido recentemente um processo importante, que trata da oxidação enzimática de compostos de boro (Esquema 3). 25 Nesse estudo explorou-se a quimiosseletividade e a enantiosseletividade de reações catalisadas por diversas Baeyer-Villiger monooxigenases (BVMO).…”

Section: A Catálise Assimétrica No Brasilunclassified

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

Braga¹,

Lüdtke²,

Schneider³

et al. 2013

Quím. Nova

View full text Add to dashboard Cite

Recebido em 11/7/13; aceito em 9/10/13; publicado na web em 24/10/13 ASYMMETRIC CATALYSIS IN BRAZIL: DEVELOPMENT AND POTENTIAL FOR ADVANCEMENT OF BRAZILIAN CHEMICAL INDUSTRY. The preparation of enantiomerically pure or enriched substances is of fundamental importance to pharmaceutical, food, agrochemical, and cosmetics industries and involves a growing market of hundreds of billions of dollars. However, most chemical processes used for their production are not environmentally friendly because in most cases, stoichiometric amounts of chiral inductors are used and substantial waste is produced. In this context, asymmetric catalysis has emerged as an efficient tool for the synthesis of enantiomerically enriched compounds using chiral catalysts. More specifically, considering the current scenario in the Brazilian chemical industry, especially that of pharmaceuticals, the immediate prospect for the use of synthetic routes developed in Brazil in an enantioselective fashion or even the discovery of new drugs is practically null. Currently, the industrial production of drugs in Brazil is primarily focused on the production of generic drugs and is basically supported by imports of intermediates from China and India. In order to change this panorama and move forward toward the gradual incorporation of genuinely Brazilian synthetic routes, strong incentive policies, especially those related to continuous funding, will be needed. These incentives could be a breakthrough once we establish several research groups working in the area of organic synthesis and on the development and application of chiral organocatalysts and ligands in asymmetric catalysis, thus contributing to boost the development of the Brazilian chemical industry. Considering these circumstances, Brazil can benefit from this opportunity because we have a wide biodiversity and a large pool of natural resources that can be used as starting materials for the production of new chiral catalysts and are creating competence in asymmetric catalysis and related areas. This may decisively contribute to the growth of chemistry in our country.Keywords: asymmetric catalysis; chiral compounds; chiral catalyst. INTRODUÇÃOCom o objetivo de fomentar e contribuir na formulação de novas políticas de C&T, especialmente para a área de Química, apresentam--se, nesse artigo, diagnósticos, reflexões e discussões sobre a atual situação da área de Catálise Assimétrica no Brasil. Propõem-se, ainda, ações que permitam à Química do País contribuir para um futuro próspero, seguro e sustentável para sua população. A presente proposta está de acordo com os position papers "Química sem Fronteiras" da Química Nova, 1 nos temas centrais: Indústria Química e Inovação, nos setores farmoquímicos, agroquímicos e de alimentos. Enquadra-se, também, nos temas transversais, nos setores de inovação e agregação de valores.Durante as últimas décadas grandes esforços vêm sendo realizados no sentido de se estabelecer rotas enantiosseletivas para a preparação de substâncias enantiomericamente puras ou enriq...

show abstract

Section: A Catálise Assimétrica No Brasilunclassified

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

Braga¹,

Lüdtke²,

Schneider³

et al. 2013

Quím. Nova

View full text Add to dashboard Cite

show abstract

“…5 Recently we initiated a program aiming at the synthesis of enantiomericaly pure naturally occurring lactones using enzymes in a deracemization step. [6][7][8] A versatile protocol introduced by us consists in the application of a methodology developed by Gutmam and coworkers, which transforms the commercially available 4-ketopimelic acid (1) into the chiral lactone (S)-(-)-2, which was transformed in our laboratory into both (S) 7 and (R) 8 isomers of jasmolactone 3, a compound with organoleptic properties, described as fruity, flowery, green, creamy, sweet and juicy 3 (Scheme 1). This strategy is interesting since the common intermediate 2 can lead to both enantiomers of a naturaly occurring γ-butyrolactone.…”

Section: Introductionmentioning

confidence: 99%

“…12 The (S) configuration of the lactone 2 was attributed by comparision of its specific rotation, [ 12 and its enantiomeric excess was determined by means of chiral HPLC. 7 Transformation of the ester function of (S)-2 into an aldehyde was achieved by deprotection of the benzyl group followed by reduction with borane-methyl sulfide complex (BMS) and oxidation with pyridinium chlorochromate (PCC). 7,12 Using this procedure, the integrity of the stereogenic center was preserved and (S)-5 was the product (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

“…7 Transformation of the ester function of (S)-2 into an aldehyde was achieved by deprotection of the benzyl group followed by reduction with borane-methyl sulfide complex (BMS) and oxidation with pyridinium chlorochromate (PCC). 7,12 Using this procedure, the integrity of the stereogenic center was preserved and (S)-5 was the product (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis of (S)-4 started with the reduction of 4-ketopimelic benzyl ester as described previously (Scheme 3). 7,12 The obtained alcohol 8 was submitted to enantioselective lactonization by PPL leading to (S)-2 in 92% e.e. 12 The (S) configuration of the lactone 2 was attributed by comparision of its specific rotation, [ 12 and its enantiomeric excess was determined by means of chiral HPLC.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A short and efficient enantioselective synthesis of (+) and (-)-(Z)-7,15-hexadecadien-4-olide: the sex pheromone of the yellowish elongate chafer, Heptophylla picea

Clososki

Ricci

Costa

et al. 2004

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Os enantiômeros (R) e (S) da Z-7,15-hexadecadien-4-olida (4), o feromônio sexual da Heptophylla picea foram sintetizados. Na etapa chave foi utilizada uma enantiolactonização já conhecida, intermediada por uma lipase, levando a um precursor comum de ambos enantiômeros do feromônio em 92% de e.e. Z-7,15-hexadecadien-4-olide (4), the sex pheromone of Heptophylla picea, were synthesized. A known lipase-catalysed enantiolactonization in the key step afforded a common precursor for both enantiomers of the pheromone in 92% e.e. The (R) and the (S) enantiomers of the

show abstract

Synthesis, Conformation and Equilibrium Study of New Piperazine and Azamacrocyclic Ligands with N-(Tetrahydro-2-oxofuran-3-yl) and N-[(Carboxy)(2-hydroxyethyl)methyl] Pendant Arms

et al. 2002

View full text Add to dashboard Cite

Enantioselective synthesis of (−)-γ-jasmolactone

Cited by 16 publications

References 13 publications

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

A short and efficient enantioselective synthesis of (+) and (-)-(Z)-7,15-hexadecadien-4-olide: the sex pheromone of the yellowish elongate chafer, Heptophylla picea

Synthesis, Conformation and Equilibrium Study of New Piperazine and Azamacrocyclic Ligands with N-(Tetrahydro-2-oxofuran-3-yl) and N-[(Carboxy)(2-hydroxyethyl)methyl] Pendant Arms

Contact Info

Product

Resources

About