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A Rapid Stereocontrolled Entry to the ABCD Tetracyclic Core of Neotuberostemonine
Author(s) -
BookerMilburn Kevin I.,
Hirst Paul,
Charmant Jonathan P. H.,
Taylor Luke H. J.
Publication year - 2003
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.200250507
Subject(s) - desymmetrization , ring (chemistry) , sn2 reaction , stereochemistry , core (optical fiber) , chemistry , lactone , enantioselective synthesis , computer science , organic chemistry , telecommunications , catalysis
Four out of the five rings of the alkaloid neotuberostemonine ( 1 ) are present in the advanced precursor 2 . The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3 . A key step in the synthesis was the cuprate‐mediated S N 2′ ring‐opening desymmetrization of the C 2 ‐symmetric bislactone 4 .