期刊
ORGANIC LETTERS
卷 22, 期 21, 页码 8697-8701出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03281
关键词
-
资金
- JSPS Research Fellowships for Young Scientists [19J12788]
- Grants-in-Aid for Scientific Research [19J12788] Funding Source: KAKEN
The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid. The bicyclic guanidine unit was constructed by the intramolecular aminal formation of an acyclic bis-guanidine derivative possessing a ketone carbonyl at C-4. From the bicyclic aminal intermediate, (+)-saxitoxin, (+)-decarbamoyl-beta-saxitoxinol [(+)-dc-beta-saxitoxinol], and the unnatural skeletal isomer, (-)-iso-dc-saxitoxinol, were synthesized.
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