Abstract
Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 910-923 |
| Number of pages | 14 |
| Journal | Chinese Journal of Chemistry |
| Volume | 18 |
| Issue number | 6 |
| DOIs | |
| State | Published - 2000 |
| Externally published | Yes |
Keywords
- Antiviral
- Julia olefination
- Macrolactin A
- Stereoselective synthesis
- Sulfone alkylation
- Wittig reaction
ASJC Scopus subject areas
- Chemistry(all)