Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.
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| Main Authors: | , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2003
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| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015 |
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