Journal article
Asymmetric syntheses of the 1-hydroxymethyl-2-hydroxy substituted pyrrolizidines (−)-macronecine, (−)-petasinecine, (−)-1-epi-macronecine, (+)-1-epi-petasinecine and (+)-2-epi-rosmarinecine
- Abstract:
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The asymmetric syntheses of all four possible diastereoisomeric 1-hydroxymethyl-2-hydroxy substituted pyrrolizidines, (−)-macronecine, (−)-petasinecine, (−)-1-epi-macronecine and (+)-1-epi-petasinecine, are reported. Conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl (E)-hepta-2,6-dienoate, followed by aldol reaction with acrolein under various conditions gave four possible diastereoisomeric β-amino esters with the required stereogenic centres installed. In each ...
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- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Accepted manuscript, pdf, 419.2KB)
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- Publisher copy:
- 10.1016/j.tet.2016.09.047
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Authors
Bibliographic Details
- Publisher:
- Elsevier Publisher's website
- Journal:
- Tetrahedron Journal website
- Volume:
- 72
- Issue:
- 47
- Pages:
- 7449-7461
- Publication date:
- 2016-09-21
- Acceptance date:
- 2016-09-20
- DOI:
- EISSN:
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1464-5416
- ISSN:
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0040-4020
- Source identifiers:
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655014
Item Description
- Keywords:
- Pubs id:
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pubs:655014
- UUID:
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uuid:298fd452-46b7-436b-a7ff-c3e29ae90d68
- Local pid:
- pubs:655014
- Deposit date:
- 2017-06-02
Terms of use
- Copyright holder:
- Elsevier Ltd
- Copyright date:
- 2016
- Notes:
- Copyright © 2016 Elsevier Ltd. This is the accepted manuscript version of the article. The final version is available online from Elsevier at: https://doi.org/10.1016/j.tet.2016.09.047
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