Synthesis of Amphidinolide E C10−C26 Fragment
2008; American Chemical Society; Volume: 10; Issue: 21 Linguagem: Inglês
10.1021/ol801923y
ISSN1523-7060
AutoresJorge Martín Esteban, Anna M. Costa, Jaume Vilarrasa,
Tópico(s)Marine Sponges and Natural Products
ResumoThe key C10-C26 fragment in a total synthesis of (-)-amphidinolide E has been prepared from an oxolane-containing C10-C17 segment (9, derived from L-glutamic acid) via a Julia-Kocienski reaction with aldehyde 3, followed by a Sharpless AD to obtain the desired diol. The C22-C26 fragment was installed by means of an efficient Suzuki-Molander coupling, with an organotrifluoroborate reagent (4, arising from a cross-metathesis reaction between a vinylboronate and 2-methyl-1,4-pentadiene).
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