Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.
[reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds.
Tinsley
Jennifer M
JM
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Mertz
Eric
E
Chong
Pek Y
PY
Rarig
Robert-André F
RA
Roush
William R
WR
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D001895:Boron / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007700:Kinetics; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D005663:Furans; D012821:Silanes; C511847:allylsilane; C061022:bullatacin; D001895:Boron; C039281:furan