Aldehyde 9 was prepared in four steps beginning with the Baeyer-Villager oxidation of 2- allylcyclopentanone (12). 14 Alkylation provided 141Za as a 1: l mixture of lactones, which in turn was protected as the ortho ester, 12a employing (+)-(R, R)-2, 3-butanediol. 15 The latter operation served not only to equilibrate the mixture to a 6: 1 trans/& mixture (15a, b/15c, d)
[Smith III, Amos B.; Leahy, James W.; Noda, Ichio; Remiszewski, Stacy W.; Liverton, Nigel J.; Zibuck, Regina Journal of the American Chemical Society, 1992 , vol. 114, # 8 p. 2995 - 3007]