Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent [3 + 2]-annulation reactions.
A convergent synthesis of the annonaceous acetogenin, 10-hydroxytrilobacin ( 4a), was accomplished by using the [3 + 2]-annulation reaction of tetrahydrofuranyl carboxaldehyde 2a and allylsilane 3. The stereodivergency of the [3 + 2]-annulation reaction made it possible to achieve modular, highly stereoselective syntheses of three 10-hydroxytrilobacin diastereomers from the same precursors by using simple modifications of reaction conditions.
Huh
Chan Woo
CW
Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
C103451:10-hydroxyasimicin; D000447:Aldehydes; D000475:Alkenes; D000480:Alkynes; D005663:Furans; D012821:Silanes; C511847:allylsilane