Several metal mediated allylations and Grignard additions to ketones 3 and 5, both derived from (R)-2,3-cylcohexylideneglyceraldehyde, took place with very high diastereoselectivity producing the same tertiary carbinol 4b as the major product. Subsequently, 4b was exploited to synthesize (+)-tanikolide efficiently through a series of simple reactions employing an RCM strategy.