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FORMATION OF HIGHLY SUBSTITUTED CYCLOPENTANES FROM RADICAL AND ANIONIC MICHAEL CYCLIZATIONS OF ALPHA-IODO-GAMMA-LACTONES AND ALPHA-IODO-DELTA-LACTONES

Abstract:
α-Iodo-δ- and -γ-hexonlactones with α,β-unsaturated esters developed from C-6 undergo both tributyltin hydride-induced radical and base catalysed anionic Michael cyclisations to form bicyclic lactones with very highly substituted homochiral cyclopentanes. The δ-lactones give cyclopentane products in which adjacent carbon substituents on the cyclopentane ring are cis to each other, whereas γ-lactones give cyclopentanes in which the carbon chains are trans. © 1994.
Publication status:
Published

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Journal:
TETRAHEDRON LETTERS
Volume:
35
Issue:
27
Pages:
4823-4826
Publication date:
1994-07-04
DOI:
ISSN:
0040-4039
URN:
uuid:d37709ec-e3c6-4ec4-8345-ac7e6a13a423
Source identifiers:
327076
Local pid:
pubs:327076
Language:
English

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