First Total Synthesis of (±)‐Rabelomycin | Zendy

Krohn Karsten | Zendy; Khanbabaee Karamali | Zendy

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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.

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