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Total Synthesis of (−)‐Enigmazole A
Author(s) -
Sakurai Keisuke,
Sasaki Makoto,
Fuwa Haruhiko
Publication year - 2018
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.201801561
Subject(s) - moiety , domino , tetrahydropyran , chemistry , intramolecular force , ring closing metathesis , total synthesis , olefin fiber , stereochemistry , olefin metathesis , metathesis , ring (chemistry) , natural product , ketone , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
Total synthesis of (−)‐enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross‐metathesis/intramolecular oxa‐Michael addition of a δ‐hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold‐catalyzed rearrangement of a propargylic benzoate, followed by ring‐closing metathesis of the resultant α,β‐unsaturated ketone.