Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F(sub 1.alpha.), -F(sub 1.beta.), -A1, and -B1 hormones

Corey, E. J.; Andersen, Niels H.; Carlson, Robert M. K.; Paust, Joachim; Vedejs, E.; Vlattas, Isidoros; Winter, Rudolph Ernst K.

doi:10.1021/ja01014a053

Cited by 186 publications

(30 citation statements)

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“…The copper-carbodimide elimination method was first reported in 1960s,11 Sai and co-workers found that this elimination method could give high syn -selective E/Z enamides 12. The utility of the copper-carbodimide method to prepare dehydroamino acids in a natural product was demonstrated in the total synthesis of roquefortine C 13…”

mentioning

confidence: 99%

A copper-carbodiimide approach to the phomopsin tripeptide side chain

Shangguan

Joullié

2009

Tetrahedron Letters

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mentioning

confidence: 99%

A copper-carbodiimide approach to the phomopsin tripeptide side chain

Shangguan

Joullié

2009

Tetrahedron Letters

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“…Diese Methode wurde durch Corey et al erstmals für die Synthese von ,-ungesätigten Ketonen aus -Hydroxyketonen beschrieben. [203] Miller nutze diese zur Synthese von Dehydroaminosäureestern, [204] und die Albericio-Gruppe weitete sie erfolgreich auf Peptide aus. [205][206][207][208] Dabei verläuft die Eliminierung über die Bildung eines iso-Harnstoffs.…”

Section: Synthese Der Peptidthiazoleunclassified

Totalsynthese von Nosiheptid

Wojtas

Riedrich

et al. 2016

Angewandte Chemie

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Eine Totalsynthese des bismakrocyclischen Thiopeptidantibiotikums Nosiheptid gelang durch den Aufbau einer voll funktionalisierten linearen Vorstufe und konsekutive Makrocyclisierungen. Schlüsselmerkmale waren eine kritische Makrothiolactonisierung und eine milde Entschützungsstrategie für den 3‐Hydroxypyridin‐Kern. Der Naturstoff war mit isoliertem authentischem Material im Hinblick auf spektroskopische Daten und antimikrobielle Aktivität identisch.

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“…11 Treatment of the major diastereoisomer 14a with dicyclohexylcarbodiimide (DCC) and cuprous chloride in refluxing toluene stereospecifically provided (E)-isobutylidene piperidinone 15a in 88% yield, while under the same conditions (Z)-isobutylidene piperidinone 15b was formed in 87% yield from the minor aldol adduct 14b.…”

Section: The Construction Of the (Z)-alkylidene Side Chain And The Symentioning

confidence: 99%

Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G

Santos¹,

Pilli²

2003

J. Braz. Chem. Soc.

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A adição de 5-metil-2-tri-isopropilsililoxifurano (5) a N-carbobenziloxi-2-metoxipiperidina (6a) forneceu uma mixtura dos isômeros eritro e treo 7a and 8a, respectivamente, em rendimentos de moderado a bom (42-85%) e razão diastereoisomérica (7a : 8a) variando entre 1,1:1 -6:1, dependendo do sistema de solvente e do ácido de Lewis empregados. O isômero treo 8a foi transformado na (+/-)-homopumiliotoxina 223G (1) que foi obtida a partir de 6a em 5 etapas e 13% de rendimento total.The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 -6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.

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Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F(sub 1.alpha.), -F(sub 1.beta.), -A1, and -B1 hormones

Cited by 186 publications

References 0 publications

A copper-carbodiimide approach to the phomopsin tripeptide side chain

A copper-carbodiimide approach to the phomopsin tripeptide side chain

Totalsynthese von Nosiheptid

Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G

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