ortho-quinone methides from para-quinones: Total synthesis of rubioncolin B

Jean Philip Lumb; Kevin C. Choong; Dirk Trauner

doi:10.1021/ja803498r

ortho-quinone methides from para-quinones: Total synthesis of rubioncolin B

Jean Philip Lumb, Kevin C. Choong, Dirk Trauner

Chemistry

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

Abstract

A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.

Original language	English (US)
Pages (from-to)	9230-9231
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	29
DOIs	https://doi.org/10.1021/ja803498r
State	Published - Jul 23 2008

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja803498r

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title = "ortho-quinone methides from para-quinones: Total synthesis of rubioncolin B",

abstract = "A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.",

author = "Lumb, {Jean Philip} and Choong, {Kevin C.} and Dirk Trauner",

year = "2008",

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doi = "10.1021/ja803498r",

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T2 - Total synthesis of rubioncolin B

AU - Lumb, Jean Philip

AU - Choong, Kevin C.

AU - Trauner, Dirk

PY - 2008/7/23

Y1 - 2008/7/23

N2 - A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.

AB - A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.

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M3 - Article

C2 - 18582058

AN - SCOPUS:47749100518

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

ortho-quinone methides from para-quinones: Total synthesis of rubioncolin B

Abstract

ASJC Scopus subject areas

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