Synthesis of a C20-C26 segment of superstolide A by addition of a chiral allenylzinc reagent to (R)-N-boc alaninal.
[reaction: see text] Additions of chiral allenylzinc and indium reagents to N-Boc alaninal were examined as a possible route to a C20-C26 segment of superstolide A. Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts.
Marshall
James A
JA
Department of Chemistry, P.O. Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Mulhearn
James J
JJ
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
C507270:(R)-N-boc alaninal; D007202:Indicators and Reagents; D018942:Macrolides; D011714:Pyrans; D013764:Tetrahydronaphthalenes; C091984:superstolide A; D000409:Alanine