ChemInform Abstract: 10‐NOR‐9,11‐SECOPROSTAGLANDINS. SYNTHESIS, STRUCTURE, AND BIOLOGY OF ENDOPEROXIDE ANALOGS

Lin, Chiu Hong; Alexander, David L.; Chidester, C. G.; Gorman, Robert R.; Johnson, Roy A.

doi:10.1002/chin.198226319

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“…The assignments of cyclohexane derivative (18) and cyclopentene derivative (19), based on signal multiplicities, are straightforward. The relative orientations of hydroxyl and alkyl groups in (18) and ( 19) are known from chemical evidence and are confirmed by 13 C chemical shifts.…”

Section: Resultsmentioning

confidence: 99%

13с NMR Spectroscopy of Prostaglandins 2. Prostanoids With Oxygen at C9 and Their Intermediates

Lille¹,

Lippmaa²,

Lopp³

et al. 1986

Proceedings of the Academy of Sciences of the Estonian SSR. Che

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PROSTAGLANDIINIDE 13 C TMR SPEKTROSKOOPIA 2. Prostanoidid hapniku aatomiga С9 juures ja nende sünteesi vaheühendid Prostaglandiinide F 2(Z , F 2 p ja E 2 , prostatsükliinide li, I 2 ja karbatsükliini I 2 konformatsioonianalüüsi ning nende ühendite 13 C keemiliste nihete uurimisega on leitud sõltuvus 5-liikmelise ringi konformatsiooni ja I3 C nihete vahel. Selgus, et konformatsiooni muutumisega eksost endoks ehk prootonite 1,3-diaksiaalse orientatsiooni kadumisega kaasneb vastavate 13 C tuumade resonantssageduse nihkumine 2-3 ppm võrra tugevamasse välja. Seda sõltuvust kasutati prostanoidide sünteesi vaheühendite konformatsiooni määramiseks. Artiklis on toodud 102 prostanoidi ja nende vaheühendite 13 C keemilised nihked (neist 37 ühendi omad esmakordselt). Korrigeeriti mitmeid kirjanduses leiduvaid tulemusi.СПЕКТРОСКОПИЯ ЯМР 1 3 C ПРОСТАГЛАНДИНОВ 2. Простаноиды с кислородом при С9 и промежуточные продукты их синтеза Анализом констант спин-спинового взаимодействия 3 Jhh' и конформаций простагландинов F 2 и Ео и ряда простациклинов установлена зависимость химических сдвигов 13 С в этих соединениях от конформации 5-членных циклов. Обнаружено, что исчезновение протон-протонной ориентации, близкой к 1,3-диаксиальной, сопровождается сильнопольным сдвигом резонансов соответствующих ядер 13 С на 2-3 м. д. Эта закономерность использована для определения конформации промежуточных продуктов синтеза простаноидов. В статье приведены химические сдвиги 13 С 102 простаноидов и их промежуточных продуктов.

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Section: Resultsmentioning

confidence: 99%

13с NMR Spectroscopy of Prostaglandins 2. Prostanoids With Oxygen at C9 and Their Intermediates

Lille¹,

Lippmaa²,

Lopp³

et al. 1986

Proceedings of the Academy of Sciences of the Estonian SSR. Che

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ChemInform Abstract: 10‐NOR‐9,11‐SECOPROSTAGLANDINS. SYNTHESIS, STRUCTURE, AND BIOLOGY OF ENDOPEROXIDE ANALOGS

Abstract: Der Prostaglandinester (I) wird in das 10‐Nor‐9,1 1‐seco‐Derivat (IIIa) übergeführt, das u.a. röntgenstrukturanalytisch charakterisiert wird.

Cited by 1 publication

References 1 publication

13с NMR Spectroscopy of Prostaglandins 2. Prostanoids With Oxygen at C9 and Their Intermediates

13с NMR Spectroscopy of Prostaglandins 2. Prostanoids With Oxygen at C9 and Their Intermediates

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