期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 25, 页码 9393-9402出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061677t
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资金
- NIGMS NIH HHS [GM 34442, R01 GM034442, R01 GM034442-15] Funding Source: Medline
- Wellcome Trust Funding Source: Medline
Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt to establish the absolute stereochemistry at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivity could not be achieved. All attempts at a pinacol cyclization or an intramolecular 6-exo-tet epoxide opening were unsuccessful because of an unfavorable A((1,3)) strain inherent in the molecule.
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