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Synlett 1997; 1997(8): 947-949
DOI: 10.1055/s-1997-964
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Efficient Synthesis of dl-Zizaene Sesquiterpenes via Tandem Radical Cyclizations of N-Aziridinylimines

Sunggak Kim* , Jae Ho Cheong
  • *Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea, E-mail: skim@sorak.kaist.ac.kr
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Publication Date:
31 December 2000 (online)

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Tandem radical cyclizations of N-aziridinylimine 7, 17 and 21 with Bu3SnH/AIBN provided bicyclo[3.2.1]octanes and tricyclo-[6.2.1.01,5]undecanes, respectively and led to the stereocontrolled synthesis of dl-zizaene and dl-khusimone.

N-aziridinylimine - tandem radical cyclization - consecutive carbon-carbon bond formation - [6.2.1.01,5]undecane - zizaene - khusimone