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Efficient Total Synthesis of Marine Alkaloid (−)‐Nakadomarin A
Author(s) -
Cheng Bin,
Wu Fufang,
Yang Xiaobao,
Zhou Yuedong,
Wan Xiaolong,
Zhai Hongbin
Publication year - 2011
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.201102101
Subject(s) - total synthesis , ring (chemistry) , stereochemistry , alkaloid , olefin fiber , chemistry , core (optical fiber) , cascade , sequence (biology) , polar , computer science , combinatorial chemistry , organic chemistry , physics , biochemistry , telecommunications , chromatography , astronomy , polymer
Z 's top : For the total synthesis of the marine alkaloid (−)‐nakadomarin A, (−)‐camphorsulfonic acid assisted, Z ‐selective, olefin RCM of a monoamine (less polar) rather than a diamine (more polar) was found to be highly practical for constructing the F ring. The ABCD‐tetracyclic core was assembled through a novel efficacious PtCl 2 ‐promoted cascade reaction sequence (see scheme).