Guaianolides : The total synthesis of (±)-estafiatin

Demuynck, M.; Devreese, A.; Clercq, Pierre J. De; Vandewalle, M.

doi:10.1016/s0040-4039(00)87380-3

Cited by 25 publications

(5 citation statements)

References 11 publications

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“…[394] Die analoge Reaktionssequenz ausgehend von 1,2-Bis(trimethylsilyloxy)cyclopenten und Cyclopentenon [390] eröffnete den Zugang zur Synthese der Guaianolide (AE )-Compressanolid [395,396] und (AE )-Estafiatin. [396,397] Eine ähnliche formale Totalsynthese von (AE )-Compressanolid nutzte eine oxidative Diolspaltung des [2+2]-Photocycloadditionsprodukts von 1,2-Diacetoxycyclopenten und 3-Methoxycarbonylcyclopent-2-enon nach Entfernung der Acetylgruppen. [398] Die Spaltung beider Bindungen a und c (Schema 67) ergibt die formalen Produkte einer Kreuzmetathese.…”

Section: Sesquiterpens (Ae )-B-himachalen (263) (Abbildung 8)unclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

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Section: Sesquiterpens (Ae )-B-himachalen (263) (Abbildung 8)unclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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“…Compound 4 was identical with naturally occurring 1 l3,13-dihydrokauniolide by comparison of their 'H-nmr spectra and [oi]d values (25). Compounds 3 and 4 are considered to be convenient synthetic intermediates of A3'4-12,6ot-guaianolides and their derivatives, such as 8,10,11,13, 16,17, 23, and 25-27. Our attention turned next to the synthesis of estafiatin [8] (37,38), which is a constituent of Artemisia mexicana, whose extracts have been used as an anthelmintic in Mexico (18). The starting material for our synthesis of 8 was diene 3 with 1 molar equivalent of -CPBA at -20°in CH2C12 gave the monoepoxides 5 and 6, in 25% and 58% yield based on recovered starting material at 60% conversion.…”

Section: And Discussionmentioning

confidence: 99%

Studies on the Synthesis of Sesquiterpene Lactones, 16. The Syntheses of 11β,13-Dihydrokauniolide, Estafiatin, Isodehydrocostuslactone, 2-Oxodesoxyligustrin, Arborescin, 1,10-Epiarborescin, 11β,13-Dihydroludartin, 8-Deoxy-11β,13-dihydrorupicolin B, 8-Deoxyrupicolin B, 3,4-Epiludartin, Ludartin, Kauniolide, Dehydroleucodin, and Leucodin

Andô¹,

Ibayashi²,

Minami³

et al. 1994

J. Nat. Prod.

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A total of eleven naturally occurring guaianolides, 1 iP,13-dihydrokauniolide, estafiatin, isodehydrocostuslactone, 2-oxodesoxyligustrin, arborescin, 1 ß,13-dihydroludartin, 8-deoxy-11 ß, 13-dihydrorupicolin B, ludartin, kauniolide, dehydroleucodin, and leucodin, and three related compounds, 1,10-epiarborescin, 8-deoxyrupicolin B, and 3,4-epiludartin, were synthesized through a common cationic intermediate A, which was derived from ( 1151)-1 ß-(mesyloxy)eudesm-3-eno-12,6a-lactone [2] by solvolytic rearrangement.The guaianolides represent one of the largest groups of sesquiterpene lactones with over 500 known naturally occurring compounds (2). Some of them have been shown to possess high antitumor (3-15), antishistosomal (3,16,17), anthelmintic (18), contraceptive (19,20), root-growth stimulatory (3,21,22), root-growth and germination inhibitory activities (3,4,(13)(14)(15)23,24), and preventive or curative activities for crop diseases (4,15). Because of the diverse biological activities of the guaianolides and since they are

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“…Starting from 1,2‐bis(trimethylsilyloxy)cyclopentene and cylopentenone,390 the equivalent reaction sequence facilitated the synthesis of the guaianolides (±)‐compressanolide395, 396 and (±)‐estafiatin 396. 397 A similar formal total synthesis of (±)‐compressanolide employed, after removal of the acetyl protecting groups, an oxidative diol cleavage of the [2+2] photocycloaddition product of 1,2‐diacetoxycyclopentene and 3‐methoxycarbonylcyclopent‐2‐enone 398…”

Section: [2+2] Photocycloadditions Of Olefinsmentioning

confidence: 99%

Corrosion News

2007

Materials & Corrosion

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Photochemical reactions contribute in a significant way to the existing repertoire of carbon–carbon bond‐forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have been employed in natural product synthesis are presented. Selected total syntheses are discussed as examples, with particular attention given to the photochemical key step and its stereoselectivity. The structural relationship between the photochemically generated molecule and the natural product is shown, and, where necessary, the consecutive reactions in the synthesis are illustrated and classified.

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Guaianolides : The total synthesis of (±)-estafiatin

Cited by 25 publications

References 11 publications

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

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