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. Author manuscript; available in PMC: 2016 May 24.
Published in final edited form as: Nat Chem. 2015 Jun 22;7(8):641–645. doi: 10.1038/nchem.2281

Figure 4. Conversion of the exo-Diels-Alder product to the natural product.

Figure 4

a, Ambient temperature dimerization of butenolide 3a produces a racemate of the exo adduct 7a; thermal dehydration requires additional heating. b, The acyclic methyl ester derivative of 3a, the ketoester 11, also dimerizes in a highly diastereoselective fashion at ambient temperature to produce the exo adduct 10a.