Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.
A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U.
Torres
Wildeliz
W
Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, P.O. Box 23346, San Juan, Puerto Rico.
Rodríguez
Raúl R
RR
Prieto
José A
JA
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D018942:Macrolides; D011422:Propionates; C525797:streptovaricin U