Premium
Atropdiastereoselective Ring Opening of Bridged, “Axial‐Prostereogenic” Biaryls: Directed Synthesis of (+)‐Ancistrocladisine
Author(s) -
Bringmann Gerhard,
Reuscher Helmut
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198916721
Subject(s) - stereocenter , atropisomer , ring (chemistry) , chemistry , nucleophile , stereochemistry , lactone , axial chirality , unit (ring theory) , enantioselective synthesis , organic chemistry , catalysis , mathematics , mathematics education
Selective twisting of lactone 1 which has a flat, “axial prostereogenic” biaryl unit to the axial stereogenic ester 2 has been accomplished by a ring‐opening reaction involving simple O‐nucleophiles. This novel principle was the key to an atropisomer‐selective synthesis of the lianene alkaloid ancistrocladisine.