Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.
作者： Dimitar B. Gotchev , Daniel L. Comins
DOI: 10.1021/JO061677T
关键词: Conjugate 、 Epoxide 、 Medicinal chemistry 、 Intramolecular force 、 Regioselectivity 、 Absolute configuration 、 Piperidine 、 Chemistry 、 Stereochemistry 、 Intramolecular reaction 、 Pinacol
摘要: Two approaches to the aza-tricyclo dodecane skeleton of (−)-FR901483 are reported. Both routes utilized a Grignard addition an N-acylpyridinium salt establish absolute stereochemistry at C-6 and highly diastereoselective conjugate allylation reaction form quaternary center C-1 natural product in excellent yield. Although desired polysubstituted piperidine intermediates were prepared regio- stereoselectively, construction C-8/C-9 bond connectivity could not be achieved. All attempts pinacol cyclization or intramolecular 6-exo-tet epoxide opening unsuccessful because unfavorable A(1,3) strain inherent molecule.
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