Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy

Albert Padwa; Drew R. Bobeck; Edwin M. Mmutlane

doi:10.3998/ark.5550190.0011.602

Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy

Albert Padwa
, Drew R. Bobeck
, Edwin M. Mmutlane

Emory University

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

10 Citations (Scopus)

Abstract

A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The required substituted piperidin-2-one needed for the eventual 1,4-dipolar cycloaddition step was prepared using an aza-Claisen rearrangement.

Original language	English
Pages (from-to)	7-21
Number of pages	15
Journal	Unknown Journal
Volume	2010
Issue number	6
DOIs	https://doi.org/10.3998/ark.5550190.0011.602
Publication status	Published - 2010
Externally published	Yes

Keywords

1,4-Dipolar
Aza-Claisen
Betaine
Cross-conjugated
Cycloaddition
Heteroaromatic
Rearrangement

ASJC Scopus subject areas

Organic Chemistry

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10.3998/ark.5550190.0011.602

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title = "Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy",

abstract = "A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The required substituted piperidin-2-one needed for the eventual 1,4-dipolar cycloaddition step was prepared using an aza-Claisen rearrangement.",

keywords = "1,4-Dipolar, Aza-Claisen, Betaine, Cross-conjugated, Cycloaddition, Heteroaromatic, Rearrangement",

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language = "English",

volume = "2010",

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AU - Padwa, Albert

AU - Bobeck, Drew R.

AU - Mmutlane, Edwin M.

PY - 2010

Y1 - 2010

N2 - A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The required substituted piperidin-2-one needed for the eventual 1,4-dipolar cycloaddition step was prepared using an aza-Claisen rearrangement.

AB - A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The required substituted piperidin-2-one needed for the eventual 1,4-dipolar cycloaddition step was prepared using an aza-Claisen rearrangement.

KW - 1,4-Dipolar

KW - Aza-Claisen

KW - Betaine

KW - Cross-conjugated

KW - Cycloaddition

KW - Heteroaromatic

KW - Rearrangement

UR - https://www.scopus.com/pages/publications/77953383757

U2 - 10.3998/ark.5550190.0011.602

DO - 10.3998/ark.5550190.0011.602

M3 - Article

AN - SCOPUS:77953383757

VL - 2010

SP - 7

EP - 21

JO - Unknown Journal

JF - Unknown Journal

IS - 6

ER -

Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy

Abstract

Keywords

ASJC Scopus subject areas

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