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Title: Stereocontrolled total synthesis of amphidinolide X via a silicon-tethered metathesis reaction. Author: Rodríguez-Escrich C, Urpí F, Vilarrasa J. Journal: Org Lett; 2008 Nov 20; 10(22):5191-4. PubMed ID: 18928293. Abstract: Two 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.[Abstract] [Full Text] [Related] [New Search]