Stereoselective reduction and cyclization of 6-methyl-2-propionyl-2,3-dihydro-4H-pyran provides brevicomin in quantitative yield as a 86:14 or a 17:83 mixture of exo and endo isomers through DIBAH reduction in ether at reflux or Zn(BH4)2 in the presence of ZnCl2 in ether at 0 °C, respectively.
J. Jun and D. G. Shin, J. Chem. Soc., Perkin Trans. 1, 1991, 956 DOI: 10.1039/P19910000956
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