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Total Synthesis of 7‐ epi ‐Pukalide and 7‐Acetylsinumaximol B
Author(s) -
McAulay Kirsten,
Clark J. Stephen
Publication year - 2017
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.201702591
Subject(s) - thioether , furan , knoevenagel condensation , ylide , sulfur , total synthesis , chemistry , alcohol , organic chemistry , stereochemistry , catalysis
Convergent total syntheses of the furanocembranoids 7‐ epi ‐pukalide and 7‐acetylsinumaximol B have been achieved using a one‐pot Knoevenagel condensation and thioether‐mediated furan‐forming reaction. Furan formation proceeds via a sulfur ylide and results in rapid introduction of structural complexity during the coupling of two highly functionalised fragments. The targets have been prepared in 16 steps from ( R )‐perillyl alcohol.