A Short Synthesis of (±)-Halenaquinone

Sutherland, Hamish S.; Souza, Fabio E. S.; Rodrigo, R.

doi:10.1021/jo010112o

Cited by 37 publications

(25 citation statements)

References 10 publications

(15 reference statements)

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“…In addition to ketenes, however, as a general precept, Diels–Alder reactions of simple o ‐benzoquinones are similarly highly challenging to achieve, not only because these highly reactive substances undergo facile polymerization through Diels–Alder processes, but also because the pericyclic process is typified by a lack of regiochemical control when successful. An elegant strategy which addresses these issues is found in an intramolecular version of the reaction, beautifully formulated in the elegant total synthesis of halenaquinone ( 216 , Scheme 33) by Rodrigo and co‐workers 110a. Thus, oxidative ketalization of 2‐methoxy‐4‐methylphenol ( 209 ) with diene alcohol 210 in the presence of BTIB led to the formation of an o ‐quinone monoketal 211 ,110b an intermediate which smoothly underwent an intramolecular Diels–Alder reaction to provide both adduct 212 and tricyclic system 213 (the product of a Cope rearrangement of 212 ).…”

Section: Daring Applications Of the Diels–alder Reaction In Total mentioning

confidence: 99%

The Diels-Alder Reaction in Total Synthesis

Nicolaou

Snyder

Montagnon

et al. 2002

Angew. Chem. Int. Ed.

1,655

778

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The Diels–Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels–Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

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Section: Daring Applications Of the Diels–alder Reaction In Total mentioning

confidence: 99%

The Diels-Alder Reaction in Total Synthesis

Nicolaou

Snyder

Montagnon

et al. 2002

Angew. Chem. Int. Ed.

1,655

778

View full text Add to dashboard Cite

show abstract

“…[202], has been synthesized both through a strategy based on an intramolecular inverse-electron-demand Diels-Alder reaction and an intramolecular Heck cyclization [203,204]. …”

Section: Diels-alder Cycloaddition Reactionmentioning

confidence: 99%

Synthetic Strategies to Terpene Quinones/Hydroquinones

Gordaliza

2012

Marine Drugs

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The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation of the most relevant quinones/hydroquinones are described.

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“…5,6 To date, two asymmetric syntheses of the molecule have been reported by Shibasaki 7 and Harada, 8 whereas a total synthesis of the racemic natural product was achieved by Rodrigo et al 9 A thiophene derivative of (()-halenaquinone (6) was recently synthesized by Wipf et al to study the contribution of the diacyl furan system to the bioactivity of the natural product. 10 Our total synthesis of (-)-halenaquinone starts with iodofuran 9 (Scheme 2), which was previously developed for our synthesis of guanacastepene E and heptemerone B.…”

mentioning

confidence: 99%