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Enantioselective Total Synthesis of the Melodinus Alkaloid (+)‐Meloscine
Author(s) -
Selig Philipp,
Bach Thorsten
Publication year - 2008
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.200800693
Subject(s) - enantioselective synthesis , total synthesis , claisen rearrangement , stereochemistry , alkaloid , metathesis , chemistry , natural product , ring closing metathesis , salt metathesis reaction , ring (chemistry) , organic chemistry , catalysis , polymerization , polymer
Enantioselective synthesis in a new light : The template‐controlled [2+2] photocycloaddition leading to product 1 is the first example of this type of reaction in natural product synthesis. In addition, a retro‐benzilic acid rearrangement (→ 2 ), a Claisen rearrangement (→ 3 ), and a ring‐closing metathesis played decisive roles in the synthesis of the alkaloid (+)‐meloscine ( 4 ).