First Synthesis of Enantiopure 1,6-Difunctionalized Dodecahydrobenz[<i>f</i>]indenes

Scaglione, Jamie B.; Rath, Nigam P.; Covey, Douglas F.

doi:10.1021/jo048561m

Cited by 16 publications

(31 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Although indenone 41 has been prepared previously, 24 we developed a new route for its synthesis from enol 30 . LiAlH 4 reduction of enol 30 formed allylic alcohol 38 25 which was subsequently acetylated to form compound 39 . Ozonolysis then gave α-acetoxyketone 40 , and reduction of compound 40 with SmI 2 , using a procedure we reported previously, 26,27 afforded the desired indenone 41 .…”

Section: Resultsmentioning

confidence: 99%

“…25,28 Each starting material was oxidized to a diketone ( 51 and 53 , Schemes 6 and 7, respectively) before the enone ring was aromatized to yield compounds 13 and 17 . The adamantyl group was then introduced to form compounds 14 and 18 .…”

Section: Resultsmentioning

confidence: 99%

“…25 Compound 30 had: 1 H NMR (300 MHz, CDCl 3 ) δ 12.30 (s, 1H), 3.75 (s, 3H), 3.58 (t, J = 7.6 Hz, 1H), 2.38–1.24 (m, 9H), 1.17 (s, 9H), 0.72 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 173.7, 172.2, 96.8, 80.0, 72.4, 51.3, 41.5, 39.8, 35.0, 32.1, 31.4, 28.8 (3 × C), 25.6, 10.5.…”

Section: Methodsmentioning

confidence: 99%

“…25 Compound 38 had: 1 H NMR (300 MHz, CDCl 3 ) δ 5.01 (d, J = 1.4 Hz, 1H), 4.72 (d, J = 1.4 Hz, 1H), 3.94–3.89 (m, 1H), 3.41 (t, J = 7.4 Hz, 1H), 2.84 (s, br, 1H), 2.26–1.08 (m, 9H), 1.07 (s, 9H), 0.59 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 148.6, 107.3, 79.1, 72.5, 72.1, 45.0, 43.9, 43.1, 35.5, 31.6, 28.6 (3 × C), 24.8, 10.7; IR (film, cm −1 ) 3357, 1651, 1362; MS (ESI) for [C 15 H 26 O 2 +Na] + : 261.2, found: 261.2.…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Structure–activity studies of non-steroid analogues structurally-related to neuroprotective estrogens

et al. 2016

Self Cite

View full text Add to dashboard Cite

Estrone and 17β-estradiol are phenolic steroids that are known to be neuroprotective in multiple models of neuronal injury. Previous studies have identified the importance of their phenolic steroid A-ring for neuroprotection and have identified ortho substituents at the C-2 and C-4 positions on the phenol ring that enhance this activity. To investigate the importance of the steroid ring system for neuroprotective activity, phenolic compounds having the cyclopent[b]anthracene, cyclopenta[b]phenanthrene, benz[f]indene, benz[e]indene, indenes linked to a phenol, and a phenolic spiro ring system were prepared. New synthetic methods were developed to make some of the cyclopent[b]anthracene analogues as well as the spiro ring system. Compounds were evaluated for their ability to protect HT-22 hippocampal neurons from glutamate neurotoxicity and their activity relative to a potent neuroprotective analogue of 17β-estradiol was determined. An adamantyl substituent placed ortho to the phenolic hydroxyl group gave neuroprotective analogues in all ring systems studied.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Structure–activity studies of non-steroid analogues structurally-related to neuroprotective estrogens

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…[16,17] Dagegen blieben unsere Bemühungen, das Hydrindanon 8 mit normalen Alkylierungsmethoden zu erzeugen, erfolglos. [18] Die Umsetzung des Ketons 8 mit K-Selectrid resultierte in einer diastereoselektiven Reduktion der Carbonylfunktion. Im Anschluss daran lieferte ein zweistufiges Protokoll, bestehend aus einer Lemieux-Johnson-Spaltung des terminalen Alkens [19] und einer Cr-basierten Oxidation des intermediä-ren Lactols, das Lacton 9, wodurch die stereoselektive Einführung der C3-Methylgruppe ermçglicht wurde.…”

unclassified

Die Totalsynthese von (−)‐Nitidasin

et al. 2014

View full text Add to dashboard Cite

Nitidasin, ein komplexes Sesterterpenoid mit einem seltenen 5-8-6-5-Kohlenstoffgerüst, wurde aus dem peruanischen Naturheilmittel "Hercampuri" isoliert und ist ein Vertreter einer kleinen Gruppe von polycyclischen Sesterterpenoiden, die eine trans-Hydrindaneinheit mit einem Isopropylsubstituenten aufweisen. Als erstes Ergebnis unseres allgemeinen Ansatzes zur Synthese solcher Naturstoffe stellen wir die Totalsynthese der Titelverbindung vor. Die Schlüssel-sequenz unserer stereoselektiven und konvergenten Route besteht aus der Addition einer komplexen Alkenyllithiumverbindung an ein trans-Hydrindanon, einer chemoselektiven Epoxidierung und einer Ringschlussmetathese.

show abstract

Hajos‐Parrish‐Eder‐Sauer‐Wiechert Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

Hajos‐Parrish‐Eder‐Sauer‐Wiechert reaction is an enantioselective aldol reaction catalyzed by (S)‐proline. This reaction has a wide application in synthetic organic chemistry and extensively explored in asymmetric aldol reaction, α‐alkylation, Mannich reaction, Michael addition of carbonyl compounds. Hajos–Parrish reaction is the asymmetric version of the Robinson annulation catalyzed by (S)‐proline. The cyclic aldol product from this reaction is known as Hajos–Parrish ketol and cyclic (S)‐enedione—(7aS)‐2,3,7,7a‐tetrahydro‐7a‐methyl‐1H‐indene‐1(5,6H)‐dione—is referred to as Hajos–Parrish ketone, Hajos‐Parrish diketone, or Hajos–Wiechert ketone. This reaction is also presumed to involve in formation of a carbinolamine intermediate and nucleophilic addition of the neutral enamine to the carbonyl group together with hydrogen transfer from the proline carboxylic acid moiety to the developing alkoxide.

show abstract

First Synthesis of Enantiopure 1,6-Difunctionalized Dodecahydrobenz[f]indenes

Cited by 16 publications

References 15 publications

Structure–activity studies of non-steroid analogues structurally-related to neuroprotective estrogens

Structure–activity studies of non-steroid analogues structurally-related to neuroprotective estrogens

Die Totalsynthese von (−)‐Nitidasin

Hajos‐Parrish‐Eder‐Sauer‐Wiechert Reaction

Contact Info

Product

Resources

About