Journal article icon

Journal article

Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination.

Abstract:
Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1021/ol3020607

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Roberts, PM More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
14
Issue:
16
Pages:
4278-4281
Publication date:
2012-08-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:75f0fae1-0f49-4cf3-9016-57b4813f3f26
Source identifiers:
345609
Local pid:
pubs:345609

Terms of use


Metrics



If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP