A general entry to guaianolides. An illustrative synthesis of (±)-compressanolide

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

doi:10.1016/0040-4039(80)88117-2

Cited by 37 publications

(7 citation statements)

References 12 publications

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“…[391] Weitere Pseudoguaianolide, die auf diese Weise synthetisiert wurden, sind (AE )-Neoambrosin, (AE )-Parthenin, (AE )-Hymenin, [392] (AE )-Carpesiolin [393] und (AE )-Hysterin. [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.…”

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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“…Many terpene natural products are characterized by five−eight or five−seven fused ring systems . Examples include precapnelladiene, ledol, and compressanolide …”

mentioning

confidence: 99%

Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide

1996

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The type two intramolecular Diels-Alder reaction (T2IMDA) is an efficient method for the formation of medium rings. The methodology is particularly effective for the construction of seven- and eight-membered rings. A strategy for the synthesis of functionalized cycloheptanes and cyclooctanes has been developed that involves a bridged to fused ring interchange. The T2IMDA provides a synthesis for rigid bridged bicyclic molecules that can be stereoselectively elaborated before ozonolysis of the bridgehead double bond. Following oxidative cleavage, aldol condensation provides fused bicyclic ring systems that otherwise are difficult to synthesize. This methodology is amenable to the synthesis of terpene natural products. This is demonstrated here through total syntheses of (+/-)-ledol and (+/-)-ledene and a formal synthesis of (+/-)-compressanolide.

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“…Other pseudoguaianolides that were synthesized in this manner are (±)‐neoambrosin,392 (±)‐parthenin,392 (±)‐hymenin,392 (±)‐carpesiolin,393 and (±)‐hysterin 394. 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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A general entry to guaianolides. An illustrative synthesis of (±)-compressanolide

Cited by 37 publications

References 12 publications

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide

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