1993
DOI: 10.1039/p19930000239
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Total synthesis of three eudesman-12,8-olides, (±)-isoalantolactone, (±)-dihydrocallitrisin and (±)-septuplinolide; structure revision of septuplinolide

Abstract: Four eudesman-I 2,8-olidesr ( f ) -isoalantolactone, () -septuplinolide and its epimeric eudesmanolide at C-4 were synthesized stereoselectively via the route involving alkylation annulation of 2-methyl-3-furoic acid and oxidation of the furan ring. It was found that the structure of septuplinolide is the C -4 epimer of the reported structure.) -dihydrocallitrisin, ( Recently, manifoldly oxygenated eudesmanolides have been isolated from different plant sources, and have been shown a wide range of biological ac… Show more

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Cited by 14 publications
(7 citation statements)
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References 29 publications
(36 reference statements)
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“…The formate ester trapping approach, referred to earlier, was employed by Tada and co-workers in the synthesis of the eudesmanolide septuplinolide (66; Scheme 10). [59] The enolate of g-butyrolactone 64 was generated using sodium hydride and trapped with ethyl formate, and the resulting aldehyde was reduced to the a-(hydroxymethyl)-g-butyrolactone 65 with sodium borohydride. Without purification, alcohol 65 was treated with tosyl chloride and base to give septuplinolide (66) in 42 % yield over the 3 steps.…”
Section: Methodsmentioning
confidence: 99%
“…The formate ester trapping approach, referred to earlier, was employed by Tada and co-workers in the synthesis of the eudesmanolide septuplinolide (66; Scheme 10). [59] The enolate of g-butyrolactone 64 was generated using sodium hydride and trapped with ethyl formate, and the resulting aldehyde was reduced to the a-(hydroxymethyl)-g-butyrolactone 65 with sodium borohydride. Without purification, alcohol 65 was treated with tosyl chloride and base to give septuplinolide (66) in 42 % yield over the 3 steps.…”
Section: Methodsmentioning
confidence: 99%
“…The molecular formula of 1 was identical to that of septuplinolide (2) and both the IR profile and the 13 C NMR spectrum of compound 1 resembled those reported for septuplinolide (2) (Tada et al, 1993).…”
Section: Resultsmentioning
confidence: 53%
“…The structure of septuplinolide (2) was previously confirmed by stereoselective synthesis as a trans decaline with C-8 cis annelation (Tada et al, 1993) and single X-ray diffraction analysis (Vargas et al, 1991). The NOEs between H-14b/H-15b and H-7a/H-8a confirmed the relative stereochemistry.…”
Section: Resultsmentioning
confidence: 61%
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“…Den bereits angesprochenen Ansatz mit Ameisensäureester als Abfangreagens nahmen Tada und Mitarbeiter für die Synthese des Eudesmanolids Septuplinolid ( 66 , Schema ) 59. Zunächst stellten sie mit Natriumhydrid das Enolat des γ‐Butyrolactons 64 her, das sie dann mit Ethylformiat abfingen.…”
Section: Synthese Von α‐Alkyliden‐γ‐butyrolactonenunclassified