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Asymmetric syntheses of the 1-hydroxymethyl-2-hydroxy substituted pyrrolizidines (−)-macronecine, (−)-petasinecine, (−)-1-epi-macronecine, (+)-1-epi-petasinecine and (+)-2-epi-rosmarinecine

Abstract:

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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Publisher copy:
10.1016/j.tet.2016.09.047

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Institution:
University of Oxford
Oxford college:
Magdalen College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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:
1464-5416
ISSN:
0040-4020
Source identifiers:
655014
Keywords:
Pubs id:
pubs:655014
UUID:
uuid:298fd452-46b7-436b-a7ff-c3e29ae90d68
Local pid:
pubs:655014
Deposit date:
2017-06-02

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