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First Total Synthesis of (±)‐Rabelomycin
Author(s) -
Krohn Karsten,
Khanbabaee Karamali
Publication year - 1994
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.199400991
Subject(s) - regioselectivity , photooxygenation , cycloaddition , chemistry , total synthesis , deprotonation , disilane , diene , group (periodic table) , stereochemistry , organic chemistry , medicinal chemistry , singlet oxygen , catalysis , oxygen , ion , natural rubber , silane
To hold the position for a labile hydroxyl group and to direct a regioselective deprotonation, the Si 2 Me 5 group is introduced in the diene component 3 , from which the antibiotic rac ‐rabelomycin ( 4 ) is accessible through cycloaddition and subsequent photooxygenation. This procedure emphasizes the usefulness of the pentamethylsilyllithium 2 , readily prepared from disilane 1 , for the synthesis of tertiary alcohols.