Molecules (Jan 2016)

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

  • Li Wang,
  • Ping-Ping Shou,
  • Si-Ping Wei,
  • Chun Zhang,
  • Shuang-Xun Li,
  • Ping-Xian Liu,
  • Xi Du,
  • Qin Wang

DOI
https://doi.org/10.3390/molecules21010112
Journal volume & issue
Vol. 21, no. 1
p. 112

Abstract

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An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.

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