Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies

Ken S. Feldman; Timothy D. Cutarelli; Romina Di Florio

doi:10.1021/jo026337w

Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies

Ken S. Feldman, Timothy D. Cutarelli, Romina Di Florio

Chemistry

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

31 Scopus citations

Abstract

The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

Original language	English (US)
Pages (from-to)	8528-8537
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	67
Issue number	24
DOIs	https://doi.org/10.1021/jo026337w
State	Published - Nov 29 2002

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo026337w

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abstract = "The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.",

author = "Feldman, \{Ken S.\} and Cutarelli, \{Timothy D.\} and \{Di Florio\}, Romina",

year = "2002",

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journal = "Journal of Organic Chemistry",

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AU - Feldman, Ken S.

AU - Cutarelli, Timothy D.

AU - Di Florio, Romina

PY - 2002/11/29

Y1 - 2002/11/29

N2 - The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

AB - The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

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JF - Journal of Organic Chemistry

IS - 24

ER -

Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies

Abstract

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