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Potentially Biomimetic Total Synthesis and Relative Stereochemical Assignment of (±)‐Gracilamine
Author(s) -
Tian Songchuan,
Zi Weiwei,
Ma Dawei
Publication year - 2012
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.201205711
Subject(s) - circumstantial evidence , intramolecular force , cycloaddition , aldehyde , total synthesis , ring (chemistry) , computer science , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , history , archaeology , catalysis
Gracil(e) : The total synthesis of gracilamine features a potentially biomimetic intramolecular [3+2] cycloaddition to assemble its two fused five‐membered rings and a debenzylation/ring‐opening reaction to obtain the aldehyde intermediate (see scheme). The success of this synthesis provides a circumstantial evidence that supports the biosynthesis pathway of gracilamine proposed previously.