Journal article

Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D.

Abstract:: Two routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawaranospirolides A and C. Alternatively, epoxidation of protected 3-(dihydropyran-2-yl)-3-arylpropanoic acids results in spirolactonisation to generate ent-sawaranospirolide C; a related acid-mediated spirocyclisation gave access to ent-sawaranospirolide D.

Publication status:: Published

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APA Style

Robertson, J., Chovatia, P., Fowler, T., Withey, J., & Woollaston, D. (2010). Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. Organic and Biomolecular Chemistry, 8(1), 226–233.

MLA Style

Robertson, J., et al. “Oxidative Spirocyclisation Routes towards the Sawaranospirolides. Synthesis of Ent-Sawaranospirolides C and D.” Organic and Biomolecular Chemistry, vol. 8, no. 1, 2010, pp. 226–33.

Chicago Style

Robertson, J, P Chovatia, T Fowler, J Withey, and D Woollaston. 2010. “Oxidative Spirocyclisation Routes towards the Sawaranospirolides. Synthesis of Ent-Sawaranospirolides C and D.” Organic and Biomolecular Chemistry 8 (1): 226–33.
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Publisher copy:: 10.1039/b918091e

Authors

+ Robertson, J More by this author

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

+ Chovatia, P More by this author

Role:: Author

+ Fowler, T More by this author

Role:: Author

+ Withey, J More by this author

Role:: Author

+ Woollaston, D More by this author

Role:: Author

Journal:: Organic and biomolecular chemistry More from this journal
Volume:: 8
Issue:: 1
Pages:: 226-233
Publication date:: 2010-01-01
DOI:: 10.1039/b918091e
EISSN:: 1477-0539
ISSN:: 1477-0520

Language:: English
Keywords:: Chamaecyparis

Oxidation-Reduction

Stereoisomerism

Spiro Compounds

Cyclization
Pubs id:: pubs:55213
UUID:: uuid:519a19b2-9d71-4236-9ea6-4422d5d22e07
Local pid:: pubs:55213
Source identifiers:: 55213
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2010

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

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