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Total Syntheses of Heimiol A, Hopeahainol D, and Constrained Analogues


  • We thank the NSF (CHE-0619638) for an X-ray diffractometer and Prof. Gerard Parkin, Wesley Sattler, and Aaron Sattler for performing all of the crystallographic analyses. We also thank Adel ElSohly for performing the calculations. Financial support was provided by Columbia University, the National Institutes of Health (R01GM84994), Bristol-Myers Squibb, Eli Lilly, the NSF (Predoctoral Fellowships to N.E.W. and S.P.B.), the ACS Division of Organic Chemistry (summer fellowship to J.J.P.), and the Research Corporation for Science Advancement (Cottrell Scholar Award to S.A.S.).


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IDSI to the rescue: Use of a carefully designed cascade process empowered by the unique reagent IDSI [(Et2SI)2Cl⋅SbCl6] provided the entire [3.2.2] bicyclic core of both targets 1 and 2 in a single, stereocontrolled operation. Use of strain energies assisted in the completion of the natural products.