Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization: Organic Letters

U. Rinner; P. Siengalewicz; T. Hudlicky

doi:10.1021/ol0169877

Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization: Organic Letters

U. Rinner, P. Siengalewicz, T. Hudlicky

University of Florida

Publikation: Beitrag in Fachzeitschrift › Artikel › Begutachtung

Abstract

(matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.

Originalsprache	Englisch
Seiten (von - bis)	115-117
Seitenumfang	3
Fachzeitschrift	Org. Lett.
Jahrgang	4
Ausgabenummer	1
DOIs	https://doi.org/10.1021/ol0169877
Publikationsstatus	Veröffentlicht - 11 Dez. 2001
Extern publiziert	Ja

Forschungsfelder

Amaryllidaceae-Alkaloide
Alkaloide
Biologische Aktivität
Stereoselektive Synthese

IMC Forschungsschwerpunkte

Materials science

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

104015 Organische Chemie

UN SDGs

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10.1021/ol0169877

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title = "Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization: Organic Letters",

abstract = "(matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.",

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author = "U. Rinner and P. Siengalewicz and T. Hudlicky",

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doi = "10.1021/ol0169877",

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journal = "Org. Lett.",

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T2 - Organic Letters

AU - Rinner, U.

AU - Siengalewicz, P.

AU - Hudlicky, T.

N1 - Export Date: 13 June 2023; Cited By: 51; Correspondence Address: T. Hudlicky; Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, United States; email: [email protected]

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Y1 - 2001/12/11

N2 - (matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.

AB - (matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.

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KW - Isoquinolines

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KW - epi 7 deoxypancratistatin

KW - epi-7-deoxypancratistatin

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KW - isoquinoline derivative

KW - angiosperm

KW - article

KW - cyclization

KW - nuclear magnetic resonance spectroscopy

KW - synthesis

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M3 - Article

SN - 1523-7060

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JO - Org. Lett.

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IS - 1

ER -

Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization: Organic Letters

Abstract

Forschungsfelder

IMC Forschungsschwerpunkte

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

UN SDGs

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