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A short and stereoselective synthesis of the (±) Prelog-Djerassi lactonic acid

✍ Scribed by Kazuhiro Maruyama; Yuji Ishihara; Yoshinori Yamamoto


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
225 KB
Volume
22
Category
Article
ISSN
0040-4039

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A synthesis of (+)-Prelog-Djerassi Lacto
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A new approach to the synthesis of Prelog-Djerassi Lactonic acid (1) is reported. A key step in this synthesis involves an lreland-Claisen rearrangement/silicon-mediated fragmentation sequence to provide the carbon framework in (1).

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## Levoglucosenone (1) was used as the starting material for short and stereoselective routes to chiral synthons for (-)d-multistriatin (2) and (+)-Prelog-Djerassi lactonic acid (3). The stereochemistry of these synthons is discussed on the basis of high-resolution 'H-n.m.r. data.