Journal article

Asymmetric synthesis of (-)-(S,S)-homaline

Abstract:: The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to methyl cinnamate to install the correct stereochemistry. Subsequent functional group manipulation of the resultant β-amino ester and Sb(OEt) 3- mediated macrolactamisation was followed by homodimerisation to give (-)-(S,S)-homaline in 18% overall yield, representing the first asymmetric, and by far the most efficient synthesis of this natural product reported to date. © 2011 Elsevier Ltd. All rights reserved.

Publication status:: Published

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APA Style

Davies, S., Lee, J., Roberts, P., Stonehouse, J., & Thomson, J. (2012). Asymmetric synthesis of (-)-(S,S)-homaline. TETRAHEDRON LETTERS, 53(9), 1119–1121.

MLA Style

Davies, S, et al. “Asymmetric Synthesis of (-)-(S,S)-Homaline.” TETRAHEDRON LETTERS, vol. 53, no. 9, 2012, pp. 1119–21.

Chicago Style

Davies, S, J Lee, P Roberts, J Stonehouse, and J Thomson. 2012. “Asymmetric Synthesis of (-)-(S,S)-Homaline.” TETRAHEDRON LETTERS 53 (9): 1119–21.
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Publisher copy:: 10.1016/j.tetlet.2011.12.088

Authors

+ Davies, S More by this author

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

+ Lee, J More by this author

Role:: Author

+ Roberts, P More by this author

Role:: Author

+ Stonehouse, J More by this author

Role:: Author

+ Thomson, J More by this author

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

Journal:: TETRAHEDRON LETTERS More from this journal
Volume:: 53
Issue:: 9
Pages:: 1119-1121
Publication date:: 2012-02-29
DOI:: 10.1016/j.tetlet.2011.12.088
EISSN:: 1873-3581
ISSN:: 0040-4039

Language:: English
Keywords:: Homalium alkaloids

Conjugate addition

Lithium amide

Asymmetric synthesis

(-)-(S,S)-Homaline
Pubs id:: pubs:341453
UUID:: uuid:06f618d1-a1c1-41c8-838d-a8fb2aa703b8
Local pid:: pubs:341453
Source identifiers:: 341453
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_06f618d1a1c141c8838da8fb2aa703b8

Terms of use

Copyright date:: 2012

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

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