Premium
The Total Synthesis of the Annonaceous Acetogenin, Muricatetrocin C
Author(s) -
Dixon Darren J.,
Ley Steven V.,
Reynolds Dominic J.
Publication year - 2002
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 - 10.1002/1521-3765(20020402)8:7<1621::aid-chem1621>3.0.co;2-8
Subject(s) - acetogenin , butenolide , total synthesis , stereochemistry , tetrahydrofuran , diol , ring (chemistry) , chemistry , organic chemistry , annonaceae , biology , botany , solvent
The total synthesis of the potential antitumour agent muricatetrocin C has provided an ideal stage for the exploitation and development of new chemistry. A convergent synthetic strategy has been realised incorporating three distinct pieces of methodology, these include a highly diastereoselective hetero‐Diels–Alder reaction to construct the butenolide terminus, an oxygen to carbon rearrangement to install the trans ‐2,5‐disubstituted tetrahydrofuran ring and a spatial desymmetrisation process to afford the anti ‐diol unit.