Synthese von threo-cis/threo-trans- und erythro-cis/erythro-trans-Dihydropalustrin. 17. Mitteilung über Schachtelhalmalkaloide
✍ Scribed by Elisabeth Wälchli-Schaer; Conrad Hans Eugster
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 532 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Synthesis of threo‐cis/threo‐trans‐ and erythro‐cis/erythro‐trans‐dihydropalustrin
The first synthesis of a threefold protected spermidine, namely ^3^‐benzyloxycarbonyl‐N^1^‐phthaloyl‐N^2^‐tosylspermidin (9) is presented. Each of the protecting groups can be removed selectively. After hydrazinolysis the resulting N^3^‐benzyloxy‐carbonyl‐N^2^‐tosylspermidine (10) has been condensed with methyl (2 E)‐cis‐7,8‐epoxy‐2‐decenoate to the threo‐cis/trans piperidines 17, and with methyl (2 E)‐trans‐7,8‐epoxy‐2‐decenoate to the erythro‐cis/trans piperidines 17, respectively. After catalytic removal of the Z group, the resulting aminoesters 13 and 18, in a melt with imidazole, underwent ring closure to the 13‐membered lactames 14 and 19, respectively. reductive deprotection of the N‐tosyl group with sodium/ammonia led to the stereoisomeric palustrines 15 and 20, respectively.