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Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System.
Sun, Tian-Wen; Liu, Dong-Dong; Wang, Kuang-Yu; Tong, Bing-Qi; Xie, Jia-Xin; Jiang, Yan-Long; Li, Yong; Zhang, Bo; Liu, Yi-Fan; Wang, Yuan-Xian; Zhang, Jia-Jun; Chen, Jia-Hua; Yang, Zhen.
Afiliação
  • Sun TW; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Liu DD; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Wang KY; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Tong BQ; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Xie JX; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Jiang YL; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Li Y; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Zhang B; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Liu YF; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Wang YX; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Zhang JJ; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Chen JH; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
  • Yang Z; State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) , College of Chemistry and the Peking University , Beijing 100871 , China.
J Org Chem ; 83(13): 6893-6906, 2018 07 06.
Article em En | MEDLINE | ID: mdl-29508610
ABSTRACT
The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson-Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: China
Texto completo
Imprimir
XML
PubMed Links
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article País de afiliação: China