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Total Synthesis of (+)‐Neopeltolide
Author(s) -
Fuwa Haruhiko,
Naito Shinya,
Goto Tomomi,
Sasaki Makoto
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801399
Subject(s) - total synthesis , tetrahydropyran , metathesis , stereochemistry , cytotoxicity , metabolite , chemistry , cancer cell lines , combinatorial chemistry , computational biology , biology , ring (chemistry) , cancer , cancer cell , biochemistry , organic chemistry , genetics , in vitro , polymerization , polymer
Rapid elaboration : (+)‐Neopeltolide, a novel marine metabolite with potent cytotoxicity against several cancer cell lines, was the target of an efficient total synthesis (see scheme). The construction of the 2,4,6‐trisubstituted tetrahydropyran substructure is based on a Suzuki–Miyaura coupling/ring‐closing metathesis sequence. BOM=benzyloxymethyl, MPM=4‐methoxyphenylmethyl, TIPS=triisopropylsilyl.