Journal article

Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins

Abstract:: Reaction of diazodiketoester 8 with glyoxylates in the presence of catalytic rhodium(n) acetate generates 6,8-dioxabicyclo[3.2.1]octanes 9 and 11 in good yield. Elaboration of 9 provides a suitable alcohol 25 for acid-catalysed rearrangement to give the 2,8-dioxabicyclo[3.2.1]octane skeleton 26 of the zaragozic acids-squalestatins. More substituted diazodiketoesters 36 and 40 also undergo highly regio- and diastereoselective cycloaddition with glyoxylates to give the cycloadducts 41,43 and 44. © The Royal Society of Chemistry 2000.

Publication status:: Published

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APA Style

Hodgson, D., Bailey, J., Villalonga-Barber, C., Drew, M., & Harrison, T. (2000). Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 20, 3432–3443.

MLA Style

Hodgson, D., et al. “Selectivity in the Cycloadditions of Carbonyl Ylides with Glyoxylates: an Approach to the Zaragozic Acids-Squalestatins.” JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, no. 20, 2000, pp. 3432–43.

Chicago Style

Hodgson, D, J Bailey, C Villalonga-Barber, M Drew, and T Harrison. 2000. “Selectivity in the Cycloadditions of Carbonyl Ylides with Glyoxylates: an Approach to the Zaragozic Acids-Squalestatins.” JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, no. 20: 3432–43.
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Publisher copy:: 10.1039/b004870o

Authors

+ Hodgson, D More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Bailey, J More by this author

Role:: Author

+ Villalonga-Barber, C More by this author

Role:: Author

+ Drew, M More by this author

Role:: Author

+ Harrison, T More by this author

Role:: Author

Journal:: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:: 20
Pages:: 3432-3443
Publication date:: 2000-01-01
DOI:: 10.1039/b004870o
EISSN:: 1364-5463
ISSN:: 1470-4358

Language:: English
Pubs id:: pubs:37602
UUID:: uuid:b4169525-a8b4-4def-a8b7-5d8caff87172
Local pid:: pubs:37602
Source identifiers:: 37602
Deposit date:: 2012-12-19

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Copyright date:: 2000

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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