Premium
Stereospecific Sulfur‐Mediated Cleavage of a Spirocyclobutanone: Synthesis of a Fully Functional Precursor to the CP Compounds
Author(s) -
Meng Dongfang,
Danishefsky Samuel J.
Publication year - 1999
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/(sici)1521-3773(19990517)38:10<1485::aid-anie1485>3.0.co;2-1
Subject(s) - ketene , chemistry , isomerization , stereospecificity , cleavage (geology) , sulfur , tandem , stereochemistry , lactone , cascade reaction , combinatorial chemistry , catalysis , organic chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , composite material
A reaction sequence made up of a Sakurai reaction, ketene cyclization, sulfur‐directed Baeyer–Villiger reaction, and tandem lactone cleavage/isomerization provided the fully functionalized core of the CP compounds. Key steps were the methanolysis of 1 , which leads via 2 to the CP precursor 3 .