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Synthesis of Allahabadolactone A.

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Title: Synthesis of Allahabadolactone A.
Authors: Kongchen Wang1, Bates, Roderick W.1 roderick@ntu.edu.sg
Source: Journal of Organic Chemistry. 12/1/2017, Vol. 82 Issue 23, p12624-12630. 7p.
Abstract: A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
An: 126580140
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  Data: Synthesis of Allahabadolactone A.
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  Data: <searchLink fieldCode="AR" term="%22Kongchen+Wang%22">Kongchen Wang</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Bates%2C+Roderick+W%2E%22">Bates, Roderick W.</searchLink><relatesTo>1</relatesTo><i> roderick@ntu.edu.sg</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 12/1/2017, Vol. 82 Issue 23, p12624-12630. 7p.
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  Label: Abstract
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  Data: A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/acs.joc.7b02368
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        Text: English
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      – TitleFull: Synthesis of Allahabadolactone A.
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              Text: 12/1/2017
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