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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
Version:
Accepted Manuscript

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Publisher copy:
10.1016/j.tet.2016.09.047

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Department:
Magdalen College
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, 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
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Pubs id:
pubs:655014
URN:
uri:298fd452-46b7-436b-a7ff-c3e29ae90d68
UUID:
uuid:298fd452-46b7-436b-a7ff-c3e29ae90d68
Local pid:
pubs:655014
Paper number:
47

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