1979
DOI: 10.1021/ja00495a064
|View full text |Cite
|
Sign up to set email alerts
|

Synthetic studies on polyether antibiotics. 4. Total synthesis of monensin. 1. Stereocontrolled synthesis of the left half of monensin

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

0
30
0
2

Year Published

2000
2000
2016
2016

Publication Types

Select...
5
2
1

Relationship

0
8

Authors

Journals

citations
Cited by 167 publications
(32 citation statements)
references
References 2 publications
0
30
0
2
Order By: Relevance
“…Beginning from the previously synthesized α-ureidodiketone 8, an enantioselective TsujiTrost allylation with difurylidene acetate 21 would install a 2-furyl group at the C2 center (22); we felt that this group could function as an amine surrogate via downstream oxidative cleavage and Curtius rearrangement. 24 Since the ideal functionality at C2 would be the amine itself, a catalytic, asymmetric Mannich reaction of 8 with a strategically configured imine such as 23 was projected to deliver diketone 24 with carbamateprotected amine installed directly at C2. 25 In both the allylation and Mannich scenarios, enantioselective formation of the C2 asymmetric center would establish the lone stereochemical element that would be responsible for all subsequent diastereoselective manipulations.…”
Section: Desymmetrization Approachmentioning
confidence: 99%
“…Beginning from the previously synthesized α-ureidodiketone 8, an enantioselective TsujiTrost allylation with difurylidene acetate 21 would install a 2-furyl group at the C2 center (22); we felt that this group could function as an amine surrogate via downstream oxidative cleavage and Curtius rearrangement. 24 Since the ideal functionality at C2 would be the amine itself, a catalytic, asymmetric Mannich reaction of 8 with a strategically configured imine such as 23 was projected to deliver diketone 24 with carbamateprotected amine installed directly at C2. 25 In both the allylation and Mannich scenarios, enantioselective formation of the C2 asymmetric center would establish the lone stereochemical element that would be responsible for all subsequent diastereoselective manipulations.…”
Section: Desymmetrization Approachmentioning
confidence: 99%
“…Outros exemplos vêm aparecendo na literatura, ampliando cons- 4 , o controle da geometria depende do tipo de ácido de Lewis escolhido. Assim, podemos escolher a metodologia que envolve a formação de par-iônico-ínti-mo, conduzindo preferencialmente à configuração relativa trans entre C 4 com C 2 e C 6 ou a metodologia que envolve a formação do par-iônico separado por solvente, que conduz preferencialmente à geometria relativa cis entre C 4 com C 2 e C 6 .…”
Section: Expansão Das Potencialidades Da Reação De Ciclização De Prinsunclassified
“…Podemos encontrá-los, por ex., em carboidratos como a glicose 1, nos anéis A e B do antibiótico Monensina 2 4 , no anel A do antibiótico 17-deoxiroflamicoína 3 5 , nos anéis A, B, C, D, E, F e G da neurotoxina Brevetoxina B 4 6 e nos anéis A, B, C e D dos anti-tumorais naturais Forboxazola 5a e 5b 7 (Figura 1). Diversas estratégias seletivas vêm sendo desenvolvidas objetivando a preparação de tetraidropiranos substituídos, podendo-se citar como exemplos, as reações de hetero-Diels-Alder [8][9][10] , reações de Michael intramoleculares [11][12][13] , ciclização de dióis e de δ-hidroxicetonas 4,14,15 , reação de iodolactonização [16][17][18] , selenoeterificação de álcoois insaturados 19 , abertura de epóxidos [20][21][22] e a reação de ciclização de Prins [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] . O objetivo deste trabalho é a apresentação das principais potencialidades e limites da reação de ciclização de Prins, pouco apresentada nos cursos formais de síntese orgânica oferecidos na graduação e pós-graduação, mas que vêm se destacando nos últimos anos como uma metodologia poderosa de escolha para preparação de vários produtos naturais que apresentam, em seu arcabouço, tetraidropiranos substituídos.…”
Section: Introductionunclassified
“…Woodward's (24-26) work in total synthesis is appreciated widely in this regard, with his synthesis of reserpine being a dramatic, albeit representative example. The development of more sophisticated principles in conformational analysis opened the door to successes in acylic stereocontrol, as demonstrated in Kishi's (27)(28)(29) pioneering work in the synthesis of monensin.…”
Section: Catalyst-controlled Stereochemical Elaboration Of Chiral Intmentioning
confidence: 99%