Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

Álvarez, Eleuterio; Diaz, M. T.; Pérez, Ricardo; Ravelo, José L.; Regueiro, Alicia; Vera, Jose A.; Zurita, Dacil; Martı́n, Julio D.

doi:10.1021/jo00089a034

Cited by 95 publications

(26 citation statements)

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“…Depending on the reaction conditions, these cascades may involve direct epoxide opening or formation of epoxonium ion intermediates, in either case producing tetrahydrofuran products in agreement with Baldwin's rules [6]. Other early reports on epoxide-opening cascades focused on rearrangements of topologically interesting polyepoxides [141][142][143][144][145][146], as well as the transannular epoxide-opening cascades of conformationally flexible polyepoxide substrates [147][148][149][150].…”

Section: Epoxide-opening Cascades In the Synthesis Of Polycyclic Polymentioning

confidence: 99%

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Vilotijević

Jamison

2011

Biomimetic Organic Synthesis

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Section: Epoxide-opening Cascades In the Synthesis Of Polycyclic Polymentioning

confidence: 99%

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Vilotijević

Jamison

2011

Biomimetic Organic Synthesis

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“…[185] Similarly, the synthesis and reactions of tetraepoxides 72 derived from (Z,Z,Z,Z)-1,4,7,10-cyclododecatetraene were reported by Parrain et al [186] Also of note are the transannular epoxide-opening reactions of diepoxides derived from nine-and ten-membered cyclic dienes that were studied by Martin et al and utilized in the synthesis of ladder polyether fragments (Figure 10 b). [187,188] 6. Epoxide-Opening Cascades in the Synthesis of Polyether Ionophores…”

Section: Epoxide-opening Cascades In the Synthesis Of Topologically Imentioning

confidence: 99%

“…[185][186][187] b) Transannular epoxide-opening cascade reaction in the synthesis of fused polyether fragments (Martin, 1994). [188] Scheme 5. Construction of the central backbone of aurodox and related epoxide-opening cascade leading to 2,5-linked bistetrahydrofuran 79 .…”

Section: Epoxide-opening Cascades In the Synthesis Of Topologically Imentioning

confidence: 99%

Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

2009

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The group of polycyclic polyether natural products is of special interest due to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, as well as extreme lethality. The polycyclic structural features of this family can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products.

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“…[183,184] untersucht und zur Synthese von Leiter-Polyether-Fragmenten verwendet wurden (Abbildung 10 b). [187,188]…”

Section: Epoxidöffnungskaskaden In Der Synthese Von Topologisch Interunclassified

Epoxidöffnungskaskaden zur Synthese polycyclischer Polyether‐Naturstoffe

Vilotijević

Jamison

2009

Angewandte Chemie

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Die polycyclischen Strukturelemente von Polyether‐Naturstoffen können in einigen Fällen bis auf ihren Ursprung in der Biosynthese zurückverfolgt werden, in anderen, weniger gut verstandenen Fällen jedoch nur auf vorgeschlagene Biosynthesewege, die spekulative Epoxidöffnungskaskaden vorsehen. In diesem Aufsatz wird zusammengefasst, wie solche Reaktionskaskaden zur Synthese polycyclischer Polyether und verwandter Naturstoffe genutzt wurden. Polycyclische Polyether‐Naturstoffe sind wegen ihrer faszinierenden Struktur und ihrer biologischen Eigenschaften von besonderem Interesse. Letztere umfassen potenziell therapeutische antibiotische und fungizide Wirkungen sowie Antikrebswirkungen und außerdem eine starke Giftwirkung bis hin zur Letalität. Die polycyclischen Strukturelemente dieser Verbindungsklasse können in einigen Fällen bis auf ihren Ursprung in der Biosynthese zurückverfolgt werden, in anderen, weniger gut verstandenen Fällen jedoch nur auf vorgeschlagene Biosynthesewege, die spekulative Epoxidöffnungskaskaden vorsehen. In diesem Aufsatz wird zusammengefasst, wie solche Reaktionskaskaden zur Synthese polycyclischer Polyether und verwandter Naturstoffe genutzt wurden.

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Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

Cited by 95 publications

References 0 publications

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

Epoxidöffnungskaskaden zur Synthese polycyclischer Polyether‐Naturstoffe

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