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Two epimerisations in the formation of oxetanes from L-rhamnose: towards oxetane-containing peptidomimetics

Abstract:

The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane β-amino acids and in deter...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY More from this journal
Volume:
11
Issue:
20
Pages:
4113-4125
Publication date:
2000-10-20
DOI:
ISSN:
0957-4166
Language:
English
Pubs id:
pubs:37668
UUID:
uuid:6828fbe8-e9fe-4170-9bd7-ea3abca7ffe1
Local pid:
pubs:37668
Source identifiers:
37668
Deposit date:
2012-12-19

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