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Synthesis 2001; 2001(3): 0393-0398
DOI: 10.1055/s-2001-11429
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First Total Synthesis and Absolute Configuration of (-)-13-Hydroxy-11,12-epoxy-neocembrene

Tao Zhang* , Tao Zhang1 , Zuosheng Liu, Yulin Li
  • *National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China; Fax + 86(9 31)8 91 22 83; E-mail: liyl@lzu.edu.cn
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Publication Date:
31 December 2001 (online)

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The first enantioselective total synthesis of (-)-13-hydroxy-11,12-epoxy-neocembrene (1), a naturally occurring cembranoid isolated from soft coral Sarcophyton trocheliophorum, was achieved via a general approach by employing intramolecular McMurry coupling as a key step from (S)-(+)-carvone. The absolute configuration of the epoxide function of 1 is concluded as (11S,12S).

cembrene diterpenoid - McMurry coupling - epoxidation - 13-hydroxy-11,12-epoxy-neocembrene - total synthesis

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