期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 42, 页码 12896-12900出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja074939x
关键词
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资金
- NHLBI NIH HHS [R01 HL025854-25, R01 HL025854-24, R01 HL025854, HL25854, R01 HL025854-23] Funding Source: Medline
- NIGMS NIH HHS [F32 GM071132, GM71132] Funding Source: Medline
Hexacyclic congeners 3 and 4 of palau'amine, which incorporate both guanidine functional groups and have the cis configuration of the azabicyclo[3-3.0]octane core, are prepared in 14 steps from cycloadduct 6. Synthetic access to these analogues allows the first direct comparison of NMR data for hexacyclic diguanidine structures having the originally proposed cis-azabicyclo[3.3. 01]octan e fragment with data for natural alkaloids of the palau'amine family. This comparison provides convincing evidence in favor of the recently proposed structural revision of these marine alkaloids, fully supporting the trans configuration of the central azabicyclo[3.3.0]octane ring system of palau'amine and congeners.
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