A New, Highly Stereoselective Synthesis of all<i>trans</i>-Geranylgeraniol

Altman, Lawrence J.; Ash, Lucienne; Marson, S.A.

doi:10.1055/s-1974-23262

Cited by 56 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…For this purpose, the benzyl ether-protected farnesol 5 11 was oxidised regioselectively at the terminal trans methyl group with SeO 2 in the presence of tert-butyl hydroperoxide to give (2E,6E,10E )-1-benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol 6. 12 The latter was converted into the chloride 7 by treatment with toluene-p-sulfonyl chloride in the presence of triethylamine and 4-dimethylaminopyridine. 13 NMR studies comprising homonuclear ( 1 H-1 H, COSY and NOESY) and heteronuclear ( 1 H-13 C, HMQC and HMBC) correlation experiments were performed on the chloride 7 in order to confirm the location of the chlorine atom on the trans terminal methyl group.…”

Section: Synthesis Of Hexacyclic Polyprenoid C 35 Hydrocarbon 1 and I...mentioning

confidence: 99%

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Grosjean

Poinsot

Charrié-Duhaut

et al. 2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

We report here on the identification of two novel hexacyclic alkanes (C 33 and C 35 ) occurring in bitumen. The C 35 compound 1 was identified by comparison with a standard obtained by synthesis involving a biomimetic protoninduced extensive cyclisation of an acyclic heptaprenoid. This cascade cyclisation allows the formation of eleven asymmetric centres present in the natural compound in only one step. The C 33 analogue 2 was identified by NMR studies after isolation from the saturated hydrocarbon fraction of a bituminous rock. Both compounds are "orphan" molecular fossils of biological lipids of unknown origin formed by the extensive cyclisation of higher regular polyprenoids.

show abstract

Section: Synthesis Of Hexacyclic Polyprenoid C 35 Hydrocarbon 1 and I...mentioning

confidence: 99%

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Grosjean

Poinsot

Charrié-Duhaut

et al. 2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

show abstract

“…The central fragment (23) of la was prepared from (R)-( -f)-citronellol, which was prepared from optically pure (R)-( +)-citronellic aicd,n) in a 21% overall yield in the conventional manner. 19…”

Section: Synthesis Of Optically Active Sphingosine Relativesmentioning

confidence: 99%

Synthesis of sphingosine relatives. Part VI. Stereocontrolled synthesis of (2R,3R,5R,13S,14R)-(+)-aplisiasphingosine, a marine terpenoid.

Umemura

Mori

1987

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

“…175"/15 Torr. Fur eine andere Hersteliungsmethode s. [12]. (5)); 1,60 (s, 3 H, H3C (8)); 1,56 (s, 6 H, CH3C(7) cis zu C(5) und H3C (3) HlC (8)); 3,90 ( 3 , 2 H, H2C(I)); 2,l (br.…”

Section: Experimenteller Teilunclassified

Synthese von [16,16,16,16′,16′,16′‐²H₆] Lycopin

Hofer

Eugster

1982

Helvetica Chimica Acta

View full text Add to dashboard Cite

Synthesis of[ 16,16,16,16,16', 16'-'H,] Lycopene 4 0018-01 9X/82/1/0365-06$01.00/0 0 1982 Schweizerische Chemische Gesellschaft 366 HELVETICA CHIMICA ACTA -Vol. 65, Fasc. I (1982) -Nr. 36 kann, lassen sich Ruckschlusse auf die Konfiguration der Faltung des acyclischen Vorlaufers ziehen [4]. Zur Erkennung der Chiralitat an C(l) von bp-, B,E-, P,y, y,y-Carotin sind in vorangegangenen Arbeiten ([ 51 [6]) alle Voraussetzungen geschaffen worden; sie bedingen eine Markierung des Vorlaufers durch Deuterium. In der vorliegenden Mitteilung wird die Synthese von [16,16,16,16',16',16'-2H,1-Lycopin beschrieben'). Da die von friiheren Autoren benutzten Methoden zur Synthese von selektiv deuterierten Carotinen und Carotinoiden [8-10],) fur unsere Zielmolekel nicht unmittelbar geeignet waren, haben wir die im Schema zusammengestellte Sequenz ausgearbeitet. Benzyl((2E)-geranyl)ather (1) wurde zuerst mit SeO, zum rohen Alkohol 2a3), hierauf mit MnO, zum Aldehyd 2b und schliesslich mit Ag,O zur Carbonsaure 2c oxydiert. Die Reinigung erfolgte auf der Ester-Stufe 2d. Nach Reduktion mit LiAID, zu 2e, Bromierung nach [ 131 (+ 2f) und erneuter Reduktion mit LiAID, wurde der deuterierte Benzyl(gerany1)ather 2g erhalten. Aus bekannten mechanistischen Griinden ist sichergestellt, dass diese Reaktionsfolge zur Deuterierung der zur ungesattigten Kette trans-standigen Methylgruppe fuhren muss4).Bemerkenswert ist der Befund, dass sich die Isotop-Isomeren 1 und 2g im Gas-Chromatogramm trennen lassen (s. Fig. I). Die deuterierte Verbindung hat die grossere Retentionszeit.

show abstract

A New, Highly Stereoselective Synthesis of alltrans-Geranylgeraniol

Cited by 56 publications

References 0 publications

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Synthesis of sphingosine relatives. Part VI. Stereocontrolled synthesis of (2R,3R,5R,13S,14R)-(+)-aplisiasphingosine, a marine terpenoid.

Synthese von [16,16,16,16′,16′,16′‐²H₆] Lycopin

Contact Info

Product

Resources

About

A New, Highly Stereoselective Synthesis of alltrans-Geranylgeraniol

Cited by 56 publications

References 0 publications

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

Synthesis of sphingosine relatives. Part VI. Stereocontrolled synthesis of (2R,3R,5R,13S,14R)-(+)-aplisiasphingosine, a marine terpenoid.

Synthese von [16,16,16,16′,16′,16′‐2H6] Lycopin

Contact Info

Product

Resources

About

Synthese von [16,16,16,16′,16′,16′‐²H₆] Lycopin