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The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes.

Abstract:

Concise asymmetric syntheses of (-)-lupinine, (+)-isoretronecanol, (+)-5-epi-tashiromine and (R,R)-1-(hydroxymethyl)octahydroindolizine (the azabicyclic core within stellettamides A-C) have been achieved in 8 steps or fewer from commercially available starting materials. The key steps in these syntheses involved the preparation of enantiopure β-amino esters, upon conjugate addition of lithium (R)-N-(p-methoxybenzyl)-N-(α-methyl-p-methoxybenzyl)amide to either ζ-chloro or ζ-hydroxy substituted...

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Publication status:
Published

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Publisher copy:
10.1039/c4ob01737d

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Publisher:
Royal Society of Chemistry
Journal:
Organic and biomolecular chemistry
Volume:
12
Issue:
45
Pages:
9223-9235
Publication date:
2014-12-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:d60cdd79-02de-4391-96dd-6b47cfe7b888
Source identifiers:
486598
Local pid:
pubs:486598
Language:
English

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