Stereoselective Conversion of Aucubin into Polyfunctionalized Tetrahydro‐1 H ‐cyclopenta[ c ]furan Glucosides
Abstract Mitsunobu reaction of 2′,3′,4′,6′,10‐penta‐ O ‐pivaloylaucubin ( 6 ) with phthalimide, triphenylphosphine, and diethyl azodicarboxylate gave (6 R )‐6‐phthalimido‐perpivaloylbartsioside ( 10 ) ( Scheme 1 ). Selective oxidation reactions performed with perpivaloylaucubin ( 12 ) yielded (1 R )...
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| Published in | Helvetica chimica acta Vol. 86; no. 1; pp. 147 - 156 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
01.01.2003
|
| Online Access | Get full text |
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| Summary: | Abstract
Mitsunobu
reaction of 2′,3′,4′,6′,10‐penta‐
O
‐pivaloylaucubin (
6
) with phthalimide, triphenylphosphine, and diethyl azodicarboxylate gave (6
R
)‐6‐phthalimido‐perpivaloylbartsioside (
10
) (
Scheme 1
). Selective oxidation reactions performed with perpivaloylaucubin (
12
) yielded (1
R
)‐ and (1
S
)‐3(
β
‐
D
‐glucopyranosyloxy)‐1
H
‐cyclopenta[
c
]furan‐1‐carboxaldehydes
13
and
14
respectively (
Scheme 2
). Similarly, perpivaloyl‐6‐epiaucubin (
9
) and
10
afforded the corresponding (1
S
)‐carboxaldehyde
15
and (1
R
)‐carboxaldehyde
16
, respectively. The protected cyclopentafuran glycosides obtained in this way are versatile synthons, which may prove useful for further chemical diversification. |
|---|---|
| ISSN: | 0018-019X 1522-2675 |
| DOI: | 10.1002/hlca.200390005 |