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A Novel Approach to Synthesis of Tricyclic Diterpenoid
  • ISSN号:1005-1511
  • 期刊名称:《合成化学》
  • 时间:0
  • 分类:O6[理学—化学]
  • 作者机构:[1]Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
  • 相关基金:supported by NSFC (QT program), NSFC (20372026), SRF for ROCS.SEM
中文摘要:

A novel approach has been found and the first total synthesis of (±)-Salvirecognine was accomplished by using it. In which intramolecular cyclization and Friedel-Crafts alkylation took place simultaneously to afford key intermediates for synthesis of aromatic tricyclic diterpenoids Scheme 1As shown in Scheme 1 intramolecular cyclization and Friedel-Crafts alkylation took place simultaneously when compound 1 was treated by PPA at 125 ℃. In which the i-propyl group was introduced to the benzene ring directly and 2 was obtained in high yield. The structure of 2 was confirmed by X-ray crystallographic analysis.Scheme 2The mechanism of this novel approach might be as shown in Scheme 2. It's may be involved two times Friedel-Crafts alkylation and once fragmentation. We tried several different substrates and the new method was not only applicable in the conventional [6.6.6] tricyclic compounds but also suitable in [6.5.6] tricyclic compounds.By using the new approach as shown in Scheme 3 the first total synthesis of Salvirecognine 4,isolated from salvia recognit was achieved.Reagents and conditions: i) PPA, 125℃, 90%; ii) BBr3, CH2Cl2, 85%; iii) AlCl2H, 95%;Scheme 3

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期刊信息
  • 《合成化学》
  • 中国科技核心期刊
  • 主管单位:四川省科学技术协会
  • 主办单位:四川省化学化工学会 中国科学院成都有机化学有限公司
  • 主编:熊成东
  • 地址:成都市武侯区人民南路四段9号
  • 邮编:610041
  • 邮箱:hchx@cioc.ac.cn
  • 电话:028-85255007
  • 国际标准刊号:ISSN:1005-1511
  • 国内统一刊号:ISSN:51-1427/O6
  • 邮发代号:62-196
  • 获奖情况:
  • 1998年上C.A千名表(803位),1999年入选《中国科学引文数据库》来源期刊,1999-2002年作为《中国学术期刊综合评价数据库》...
  • 国内外数据库收录:
  • 美国化学文摘(网络版),中国中国科技核心期刊,中国北大核心期刊(2008版),中国北大核心期刊(2011版),英国英国皇家化学学会文摘
  • 被引量:7579