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Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity
Author(s) -
Maezaki Naoyoshi,
Tominaga Hiroaki,
Kojima Naoto,
Yanai Minori,
Urabe Daisuke,
Ueki Risa,
Tanaka Tetsuaki,
Yamori Takao
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500462
Subject(s) - sonogashira coupling , aldehyde , alkynylation , total synthesis , chemistry , stereochemistry , lactone , yield (engineering) , cytotoxicity , combinatorial chemistry , organic chemistry , palladium , biochemistry , in vitro , materials science , catalysis , metallurgy
Abstract Convergent total syntheses of murisolin ( 1 ), natural 16,19‐ cis ‐murisolin 2 , and unnatural 16,19‐ cis ‐murisolin 3 were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds 1 – 3 were also investigated.