Abstract
A six-step synthesis of dl-ancistrofuran (1) and its C-2 epimer (31) which involves a mercuric ion initiated diene cyclization of homogeranic acid to give lactone 16 and the phenylselenenyl chloride induced cyclization of alkylidene lactone 19 has been achieved. Also of interest are the zinc chloride assisted aldol condensation of 17 with α-(phenylthio)-γ-butyrolactone enolate anion to generate 29 and the use of ene adducts of 27 as substrates for cyclization to tetrahydrofurans 25 and 26.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1198-1205 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 46 |
| Issue number | 6 |
| DOIs | |
| State | Published - Mar 1981 |