A Concise Synthesis of Siphonodictidine

Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with ω-bromogeranyl acetate 7 gave the key γ-lactone interme...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-08, Vol.67 (8), p.1383-1386
Main Authors: Jefford, Charles W, Rossier, Jean-Claude, Boukouvalas, John, Sledeski, Adam W, Huang, Ping-Zhong
Format: Article
Language:English
Subjects:
Alkylation
Animals
Catalysis
Chemistry
Exact sciences and technology
Furans - chemical synthesis
Furans - chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Indicators and Reagents
Molecular Structure
Organic chemistry
Organosilicon Compounds - chemistry
Porifera - chemistry
Preparations and properties
Sesquiterpenes - analysis
Sesquiterpenes - chemical synthesis
Stereoisomerism
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Summary:Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with ω-bromogeranyl acetate 7 gave the key γ-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0400860