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

28 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

Access to Document

10.1021/jo026337w

Cite this

@article{a7a54cbfc0584f57812b413d48d04503,

title = "Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies",

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",

month = nov,

day = "29",

doi = "10.1021/jo026337w",

language = "English (US)",

volume = "67",

pages = "8528--8537",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies

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.

UR - http://www.scopus.com/inward/record.url?scp=0037195749&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037195749&partnerID=8YFLogxK

U2 - 10.1021/jo026337w

DO - 10.1021/jo026337w

M3 - Article

C2 - 12444635

AN - SCOPUS:0037195749

SN - 0022-3263

VL - 67

SP - 8528

EP - 8537

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this