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Asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine

Abstract:

Short and concise total asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine are reported. Oxidative cleavage of tert-butyl (S,S,S,Z)-7-[N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1- carboxylate, followed by hydrogenolysis promoted in situ cyclisation/reduction, which provided rapid access to the bicyclic core within (-)-isoretronecanol. Analogous treatment of the C(1)-epimer gave (-)-trachelantamidine. Overall, the syntheses of (-)-isoretronecanol and (-)-trachelantami...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2013.11.094

Authors


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
Journal:
TETRAHEDRON
Volume:
70
Issue:
2
Pages:
204-211
Publication date:
2014-01-14
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Source identifiers:
444619
Language:
English
Keywords:
Pubs id:
pubs:444619
UUID:
uuid:1ee42f7f-8003-48be-a406-4f50111ea1f9
Local pid:
pubs:444619
Deposit date:
2014-02-08

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