A new synthesis of stevastelin C3 (
3), a [13]-membered ring component of the stevastelin family, whose structure was recently revised, is reported. Initially, a macrolactonization approach was attempted to generate the [13]-membered macrolactone but this met with failure, so a translactonization reaction was tried to obtain the targeted stevastelin C3 (
3) from the corresponding [15]-membered ring counterpart. Unfortunately, this strategy did not prove successful, and, consequently, we opted to undertake a transesterification reaction from
23, as a means to accommodate the requisite aminoacid moiety at the correct position, to obtain
24. From
24, and through intermediates
25-
28, the acyclic precursor of the [13]-membered ring macrolactone, compound
30, was efficiently prepared. By utilizing the synthetic course developed by Chida, we took
30 forward and completed the total synthesis of stevastelin C3 (
3).
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