Lythraceous alkaloids. Part 11. Total synthesis of (±)-lythranidine
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1066-1069
- https://doi.org/10.1039/p19800001066
Abstract
The total synthesis of (±)-lythranidine (1), a cyclophane alkaloid from Lythrum anceps Makino, has been achieved through a sequence of reactions including the following key steps : the Wittig reaction of an ylide (6) with a dialdehyde (3), epimerisation of a cis-2,6-disubstituted piperidine into the desired trans-isomer through the N-nitroso-derivative (11), amidoacetalisation of a mixture of stereoisomeric diols (12) to isolate the desired compound (13), and its partial demethylation followed by hydrolysis.Keywords
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- Total synthesis of (.+-.)-decamine. A convenient scheme for the synthesis of cis- and trans-quinolizidine alkaloidsThe Journal of Organic Chemistry, 1977