| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5221583 | Tetrahedron | 2010 | 7 Pages |
Naturally occurring (1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A6, 2] together with unnatural (1S,2R,3R,7aS)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine [(+)-7a-epi-hyacinthacine A1, 3] and (1S,2R,3R,5S,7aS)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-5,7a-diepi-hyacinthacine A6, 4] have been synthesized from a DALDP derivative [5, (2R,3S,4R,5R)-3,4-dibenzyloxy-2â²-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine], as the homochiral starting material. The synthetic process employed took advantages of Wittig methodology followed by internal lactamization, in the case of (+)-7a-epi-hyacinthacine A1 (3), and reductive amination for (+)-hyacinthacine A6 (2) and (+)-5,7a-diepi-hyacinthacine A6 (4).
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