The regio‐selective four step synthesis of (1S,2R,3S,4R)‐4,7,7‐trimethyl‐3‐(neopentyloxy)bicyclo[2.2.1]heptan‐2‐ol, as recognized efficient chiral auxiliary, is presented. The strategy based on opening of the key acetal 15 (=(2S,3aR,4S,7...
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https://www.riss.kr/link?id=O111707277
2021년
-
0018-019X
1522-2675
SCI;SCIE;SCOPUS
학술저널
n/a-n/a [※수록면이 p5 이하이면, Review, Columns, Editor's Note, Abstract 등일 경우가 있습니다.]
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
The regio‐selective four step synthesis of (1S,2R,3S,4R)‐4,7,7‐trimethyl‐3‐(neopentyloxy)bicyclo[2.2.1]heptan‐2‐ol, as recognized efficient chiral auxiliary, is presented. The strategy based on opening of the key acetal 15 (=(2S,3aR,4S,7...
The regio‐selective four step synthesis of (1S,2R,3S,4R)‐4,7,7‐trimethyl‐3‐(neopentyloxy)bicyclo[2.2.1]heptan‐2‐ol, as recognized efficient chiral auxiliary, is presented. The strategy based on opening of the key acetal 15 (=(2S,3aR,4S,7R,7aS)‐2‐tert‐butyl‐4,8,8‐trimethylhexahydro‐2H‐4,7‐methano‐1,3‐benzodioxole) thus circumvents the poor reactivity of the neopentyl electrophile under alkylation conditions. Following the same strategy, but using the unreported acetal 22 (=(2R,3aS,4S,7R,7aR)‐2‐tert‐butyl‐4,8,8‐trimethylhexahydro‐2H‐4,7‐methano‐1,3‐benzodioxole), the corresponding unreported bis‐endo alcohol 23 (=(1R,2R,3S,4S)‐3‐(2,2‐dimethylpropoxy)‐4,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ol) could be isolated only in poor yield. An alternative regioselective synthesis, including an ultimate endo‐reduction remains to be found. Several erroneous chiroptical properties from the literature are corrected.
Cover Picture: (Helv. Chim. Acta 11/2021)
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