Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1929-1932Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409475
Keywords
macrocycles; metathesis; natural products; protecting groups; total synthesis
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Funding
- CNRS (France)
- EPFL (Switzerland)
- Ministere de l'Enseignement Superieur et de la Recherche
- ICSN
- Swiss National Science Foundation (SNSF)
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An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1)Browns enantioselective alkoxyallylboration and allylation of aldehydes, 2)chain elongation by iterative Horner-Wadsworth-Emmons olefination, 3)Evans' aldol reaction and 4)an ene-diene ring-closing metathesis. A neighboring-group-assisted chemoselective reductive desilylation was uncovered in this study and was instrumental to the realization of the present synthesis.
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