SYNTHESIS AND ABSOLUTE CONFIGURATION OF (−)-D3-TRITWISTANE, (−)-(1S,3S,6S,7S,10S,12S)PENTACYCLO[8.4.0.02,7.03,12.06,11]TETRADECANE
作者： Masao Nakazaki , Koichiro Naemura , Hiroaki Chikamatsu , Masami Iwasaki , Masaki Hashimoto
DOI: 10.1246/CL.1980.1571
关键词: Incubation 、 Rhodotorula rubra 、 Chemistry 、 Tetradecane 、 Absolute configuration 、 Ring (chemistry) 、 Diazomethane 、 Stereochemistry
摘要: Diazomethane ring expansion of 12-acetoxy-C2-bismethanotwistan-8-one (11) followed by the Wolff–Kishner reduction and Jones oxidation gave C2-methanoditwistan-4-one (14) whose incubation with Rhodotorula rubra afforded (−)-enantiomer 16, which was converted into (−)-(1S,3S,6S,7S,10S,12S)-D3,-tritwistane (7).
csj.jp参考文章(2)
Masao Nakazaki, Koichiro Naemura, Nobumasa Arashiba, Masami Iwasaki, Syntheses of novel gyrochiral pentacyclic systems with C2 symmetry. (-)-C2-Bismethanotwistane and (.+-.)-C2-methanoditwistane Journal of Organic Chemistry. ,vol. 10, pp. 2433- 2438 ,(1979) , 10.1021/JO01328A021
Masao Nakazaki, Koichiro Naemura, Seiichi Nakahara, Absolute configurations and absolute rotations of C2-bishomocubane, ditwist-brendane, and twistane Journal of Organic Chemistry. ,vol. 10, pp. 4745- 4750 ,(1978) , 10.1021/JO00419A009