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A practical total synthesis of racemic nyasol (7) was explored. The α-hydroxyketo compound3was prepared from commercially available starting materials in two steps. Chelation-controlled reduction of the α-hydroxyketo compound3with Zn(BH4)2gave the anti-1,2-diol compound4as the major product (anti/syn = 11.5:1). Stereospecific elimination reaction of a 1,3-cyclic thionocarbonate intermediate (5) exclusively yielded the Z-alkene compound6. Our total synthesis is very concise (seven steps), uses commercially available starting materials, and offers good overall yield (40%). [ABSTRACT FROM PUBLISHER]