Journal article

Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless Asymmetric Dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4

Abstract:: Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C–C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubstituted homoallylic alcohol. Subsequent acid-catalysed cyclisation afforded the desired [5,6]-bicyclic ketal of the target molecule. This methodology was shown to be compatible with the desired E ring fragment 35 in order to construct the CDE fragment 37 of pectenotoxin-4.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Richardson, M., Tame, C., Poole, D., & Donohoe, T. (2019). Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless Asymmetric Dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4. Chemical Science, 10(2019).

MLA Style

Richardson, M., et al. “Rhodium-Catalysed Vinyl 1,4-Conjugate Addition Coupled with Sharpless Asymmetric Dihydroxylation in the Synthesis of the CDE Ring Fragment of Pectenotoxin-4.” Chemical Science, vol. 10, no. 2019, Royal Society of Chemistry, 2019.

Chicago Style

Richardson, M, C Tame, D Poole, and T Donohoe. 2019. “Rhodium-Catalysed Vinyl 1,4-Conjugate Addition Coupled with Sharpless Asymmetric Dihydroxylation in the Synthesis of the CDE Ring Fragment of Pectenotoxin-4.” Chemical Science 10 (2019).
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Files:: ChemSci Rev.pdf

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Publisher copy:: 10.1039/C9SC01761E

Authors

+ Richardson, M More by this author

Role:: Author

+ Tame, C More by this author

Role:: Author

+ Poole, D More by this author

Role:: Author

+ Donohoe, T More by this author

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

Publisher:: Royal Society of Chemistry
Journal:: Chemical Science More from this journal
Volume:: 10
Issue:: 2019
Article number:: 6336
Publication date:: 2019-05-24
Acceptance date:: 2019-05-17
DOI:: 10.1039/C9SC01761E
EISSN:: 2041-6539
ISSN:: 2041-6520

Pubs id:: pubs:999020
UUID:: uuid:84aa67b7-a170-4f8b-a571-9000a0bf59ef
Local pid:: pubs:999020
Source identifiers:: 999020
Deposit date:: 2019-05-17

Terms of use

Copyright holder:: The Royal Society of Chemistry
Copyright date:: 2019
Notes:: © The Royal Society of Chemistry 2019. Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Licence:: CC Attribution (CC BY)

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