Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

Derek Fischer; Thong X. Nguyen; Lynnie Trzoss; Marianna Dakanali; Emmanuel A. Theodorakis

doi:10.1016/j.tetlet.2011.07.054

Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

Derek Fischer, Thong X. Nguyen, Lynnie Trzoss, Marianna Dakanali, Emmanuel A. Theodorakis

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.

Original language	English (US)
Pages (from-to)	4920-4923
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2011.07.054
State	Published - Sep 21 2011

Keywords

Aminodiene
Cycloaddition
Diels-Alder reaction
Stille coupling
Zoanthamine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.07.054

Cite this

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title = "Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids",

abstract = "Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.",

keywords = "Aminodiene, Cycloaddition, Diels-Alder reaction, Stille coupling, Zoanthamine",

author = "Derek Fischer and Nguyen, {Thong X.} and Lynnie Trzoss and Marianna Dakanali and Theodorakis, {Emmanuel A.}",

note = "Funding Information: We gratefully acknowledge the National Institutes of Health (NIH) for financial support of this work through Grant Number R01 GM081484 . We thank the National Science Foundation for instrumentation grants CHE9709183 and CHE0741968 . We also thank Dr. Anthony Mrse (UCSD NMR Facility); Dr. Yongxuan Su (UCSD MS Facility) and Dr. Arnold L. Rheingold and Dr. Curtis E. Moore (UCSD X-Ray facility). ",

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T1 - Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

AU - Fischer, Derek

AU - Nguyen, Thong X.

AU - Trzoss, Lynnie

AU - Dakanali, Marianna

AU - Theodorakis, Emmanuel A.

N1 - Funding Information: We gratefully acknowledge the National Institutes of Health (NIH) for financial support of this work through Grant Number R01 GM081484 . We thank the National Science Foundation for instrumentation grants CHE9709183 and CHE0741968 . We also thank Dr. Anthony Mrse (UCSD NMR Facility); Dr. Yongxuan Su (UCSD MS Facility) and Dr. Arnold L. Rheingold and Dr. Curtis E. Moore (UCSD X-Ray facility).

PY - 2011/9/21

Y1 - 2011/9/21

N2 - Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.

AB - Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.

KW - Aminodiene

KW - Cycloaddition

KW - Diels-Alder reaction

KW - Stille coupling

KW - Zoanthamine

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JO - Tetrahedron Letters

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Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

Abstract

Keywords

ASJC Scopus subject areas

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