Naphthalene Analogues of Lignans

The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-02, Vol.68 (3), p.854-864
Main Authors: Madrigal, Blanca, Puebla, Pilar, Peláez, Rafael, Caballero, Esther, Medarde, Manuel
Format: Article
Language:English
Subjects:
Carbazoles - chemical synthesis
Carbazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic - methods
Cyclization
Esterification
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Indicators and Reagents
Lignans - chemical synthesis
Lignans - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Organic chemistry
Podophyllotoxin - chemical synthesis
Podophyllotoxin - chemistry
Preparations and properties
Stereoisomerism
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Summary:The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0263364