Abstract
D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.
Original language | English (US) |
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Pages (from-to) | 1183-1187 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 57 |
Issue number | 7 |
DOIs | |
State | Published - Feb 11 2001 |
Keywords
- D-glucal
- Eleutheside
- Epoxide
- Hexenulose
- Stereoselective
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery