Journal article
Synthesis of 7-Deoxypancratistatin from Carbohydrates by the Use of Olefin Metathesis
The stereocontrolled synthesis of (+)-7-deoxypancratistatin is described. The convergent synthesis has been achieved by two different strategies, both of which commence from a pentose and piperonal. The latter is converted into allylic bromide 7, which is then coupled with a protected methyl 5-deoxy-5-iodo-D-ribofuranoside in the presence of zinc metal.
The first strategy involves a total of only 13 steps from D-ribose and piperonal, but suffers from a low yield in the zinc-mediated reaction between ribofuranoside 9, benzylamine, and bromide 7. The second strategy involves a total of 18 steps from D-xylose and piperonal. The former is converted into ribofuranoside 28, which is coupled with bromide 7 in the presence of zinc, and this is followed by ring-closing olefin metathesis.
Subsequent Overman rearrangement, dihydroxylation, and deprotection then affords the natural product.
Language: | English |
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Publisher: | WILEY-VCH Verlag |
Year: | 2006 |
Pages: | 3243-3253 |
ISSN: | 15213765 and 09476539 |
Types: | Journal article |
DOI: | 10.1002/chem.200501429 |
ORCIDs: | Madsen, Robert |