Radical Mediated Intramolecular [3-Atom + 2-Atom] Addition and the Synthesis of (±)-Rocaglamide: Model Studies

Ken S. Feldman; Christopher J. Burns

doi:10.1021/jo00015a008

Radical Mediated Intramolecular [3-Atom + 2-Atom] Addition and the Synthesis of (±)-Rocaglamide: Model Studies

Ken S. Feldman
, Christopher J. Burns

Chemistry

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

47 Scopus citations

Abstract

The cyclopenta[b]benzofuran ring system of the antileukemic natural product rocaglamide can be efficiently prepared by intramolecular [3 + 2] radical mediated addition. The stereochemical relationship that emerges between C(2) and C(3a) upon cyclization is identical with that seen in the natural product.

Original language	English (US)
Pages (from-to)	4601-4602
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	56
Issue number	15
DOIs	https://doi.org/10.1021/jo00015a008
State	Published - Jul 1 1991

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00015a008

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title = "Radical Mediated Intramolecular [3-Atom + 2-Atom] Addition and the Synthesis of (±)-Rocaglamide: Model Studies",

abstract = "The cyclopenta[b]benzofuran ring system of the antileukemic natural product rocaglamide can be efficiently prepared by intramolecular [3 + 2] radical mediated addition. The stereochemical relationship that emerges between C(2) and C(3a) upon cyclization is identical with that seen in the natural product.",

author = "Feldman, \{Ken S.\} and Burns, \{Christopher J.\}",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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AU - Feldman, Ken S.

AU - Burns, Christopher J.

PY - 1991/7/1

Y1 - 1991/7/1

N2 - The cyclopenta[b]benzofuran ring system of the antileukemic natural product rocaglamide can be efficiently prepared by intramolecular [3 + 2] radical mediated addition. The stereochemical relationship that emerges between C(2) and C(3a) upon cyclization is identical with that seen in the natural product.

AB - The cyclopenta[b]benzofuran ring system of the antileukemic natural product rocaglamide can be efficiently prepared by intramolecular [3 + 2] radical mediated addition. The stereochemical relationship that emerges between C(2) and C(3a) upon cyclization is identical with that seen in the natural product.

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UR - https://www.scopus.com/pages/publications/0025831531#tab=citedBy

U2 - 10.1021/jo00015a008

DO - 10.1021/jo00015a008

M3 - Article

AN - SCOPUS:0025831531

SN - 0022-3263

VL - 56

SP - 4601

EP - 4602

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Radical Mediated Intramolecular [3-Atom + 2-Atom] Addition and the Synthesis of (±)-Rocaglamide: Model Studies

Abstract

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