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Total Synthesis of Lankacyclinol
Author(s) -
Williams David R.,
Cortez Guillermo S.,
Bogen Stéphane L.,
Rojas Christian M.
Publication year - 2000
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 - 10.1002/1521-3773(20001215)39:24<4612::aid-anie4612>3.0.co;2-c
Subject(s) - intramolecular force , chemistry , metathesis , ring closing metathesis , diene , stereochemistry , combinatorial chemistry , barium hydroxide , ring (chemistry) , organic chemistry , polymerization , natural rubber , polymer
An antitumor agent from various Streptomyces species , the title compound 1 , has been synthesized for the first time, as described here. Key steps involved include a ring‐closing metathesis, a photochemically induced acylnitrene insertion process, and highly selective Julia olefinations for the preparation of E , E diene moieties. The macrocycle was formed from an intramolecular Horner‐Wadsworth‐Emmons olefination induced by barium hydroxide.