Stereocontrolled Total Synthesis of Amphidinolide X via a Silicon-Tethered Metathesis Reaction
2008; American Chemical Society; Volume: 10; Issue: 22 Linguagem: Inglês
10.1021/ol8021676
ISSN1523-7060
AutoresCarles Rodríguez‐Escrich, Fèlix Urpı́, Jaume Vilarrasa,
Tópico(s)Model-Driven Software Engineering Techniques
ResumoTwo esterifications and an RCM to create the challenging trisubstituted C12−C13 double bond were required in the total synthesis of amphidinolide X (1) reported here. Assembling the three fragments in this order, no RCM occurred or the process yielded mainly isomer Z. However, generating the E double bond first, by a new variant of a Si-tethered metathesis (using Schrock's catalyst), and carrying out the esterification and macrolactonization steps later, 1 was obtained exclusively.
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