𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of a hybrid analog of the esperamicin and dynemicin cores

✍ Scribed by Harold Mastalerz; Terrence W Doyle; John F Kadow; Dolatrai M Vyas

Book ID
104255807
Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
223 KB
Volume
37
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

An enediyne analog (2, R=H) that is a hybrid of the core structures of esperamicin and dynemicin was prepared. The key step in its synthesis was a Reissert-type reaction that involved intramolecular addition of the anion of a Z-1,3-diyn-2-ene to an N-acyl tetrahydrophenathridinium intermediate. It was found that 2 (R=H) readily undergoes epoxide rearrangement to an allylic alcohol (16). Both 2 (R=H) and 16 form the same cycloaromatized product 17 when heated in MeOH at 45 Β°C.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Synthesis of a Hybr
ChemInform Abstract: Synthesis of a Hybrid Analogue of the Esperamicin and Dynemicin Cores.
✍ H. MASTALERZ; T. W. DOYLE; J. F. KADOW; D. M. VYAS πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 31 KB πŸ‘ 2 views

## Synthesis of a Hybrid Analogue of the Esperamicin and Dynemicin Cores. -The compound (VI) represents an enediyne analogue hybrid of the core structures of esperamicin and dynemicin. Key step in the sequence is the intramolecular Reissert-type reaction of the anion of the Z-1,3-diyn-2-ene (III)

Synthesis of an esperamicin core analog
Synthesis of an esperamicin core analog with an epoxide trigger
✍ Harold Mastalerz; Terrence W Doyle; John F Kadow; Dolatrai M Vyas πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 French βš– 198 KB

An esperamicin core analog 4 with an epoxide trigger like that found in the related enediyne, dynemicin, was prepared. Surprisingly, it was found to be relatively stable; the p-aminophenyl substituent did not facilitate epoxide solvolysis to the extent that had been anticipated. A mild acid, pyridin

Design and Synthesis of Dynemicin Analog
Design and Synthesis of Dynemicin Analogs
✍ Martin E. Maier; Folkert Boße; AndrΓ© J. Niestroj πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 430 KB πŸ‘ 2 views

Dynemicin A is a member of the family of enediyne natural the enediyne, and the oxirane ring but lack the nitrogen heterocycle. In these compounds the aryl ring assumes a products. It is unique in that it combines a ten-membered enediyne with an anthraquinone substructure. These different conformati