The Winstein rearrangement is unique among [3,3]sigmatropic rearrangements in that it occurs at or even below room temperature. Although it has seldom been applied in total synthesis, there have been recent advances in both mechanistic understanding and synthetic applications. The equilibrium is influenced by factors that include conjugation, syn-pentane interactions, stereoelectronic effects and alkene substitution. In the proposed Winstein rearrangement, we reasoned formation of the thermodynamically more stable trisubstituted alkene in 11b would drive the reaction. The formation of 11b could also relieve steric strain, as 11a contains three contiguous quaternary centers whereas 11b has only two. It is worth highlighting that our failed sequential rearrangements (Scheme 1) both occurred in the presence of the urea; thus, we felt performing both rearrangements sequentially might circumvent off-target reactivity by delaying urea formation until the C2 stereocenter is installed. The forward synthesis commenced from protected alanine 15 (Scheme 3). An aldol reaction with 16 using LDA and SnCl2 furnished 17 in 87% yield and 15:1 dr, likely due to the greater coordinating ability of a tin enolate compared to lithium. The newly formed secondary alcohol was protected with a TBS group and the benzyl ester converted to the methyl ketone of 18. The stereochemistry of the C5 quaternary center was set by the addition of a vinyl Grignard reagent to 18 in the presence of LaCl3-2LiCl to deliver 13 in 79% yield and >20:1 following alcohol deprotection. Attempts to perform this organometallic addition in the absence of CH2Cl2 resulted in recovered 18. A RRCM furnished cyclopentene 19, although an initial TBS deprotection was necessary. Next, the C4 amine was converted to a tertiary azide via SES-deprotection with CsF and azide transfer with triflic azide to furnish 20 in 74% yield over two steps. A series of protecting group manipulations, followed by transformation of the C3 alcohol to a carbamate, gave the Ichikawa/Winstein rearrangement precursor 11. Scheme 3. Synthesis of the Ichikawa precursor 11.