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| Titel: |
Total Synthesis of Antibiotic A23187 (Calcimycin) from D-Glucose: Communication |
| Auteur: |
Nakahara, Yoshiaki Fujita, Akira Ogawa, Tomoya |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 3 (1984) nr. 3 pagina's 487-492 |
| Jaar: |
1984 |
| Inhoud: |
Antibiotic A23187 [image omitted] 1 is a cation ionophore highly specific for Ca2+. Because of its unique dioxaspiro ring structure as well as its biological activities,2 several synthetic approaches to the compound have been reported.3 We report here the first example of the total synthesis of [image omitted] based on the use of a carbohydrate template.4 The target structure [image omitted] was synthesized from the chiral synthons or “chirons”5 [image omitted] and [image omitted] via a key intermediate [image omitted] , as shown in Scheme I. A thermodynamically controlled, acid catalyzed ring closure of [image omitted] was expected to provide a correct configuration at the spiro center C-14 according to the anomeric effect.6 The two chirons [image omitted] and [image omitted] were prepared from [image omitted] -glucose via the same intermediate [image omitted] -as follows (Scheme II). |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 245 van 252 gevonden artikelen
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