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Published April 2016 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol


The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting-group strategy led to the modification of this approach beginning with (±)-glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero-Diels–Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition into the corresponding enone synthon. Addition of a model alkyne provides support for the late-stage addition of a hindered alkyne to the caprolactam building block.

Additional Information

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 26, 2016; Article first published online: 19 APR 2016. The authors wish to thank the NIH-NIGMS (R01GM080269), the Tobacco Related Disease Research Program (Fellowship to J. T. B.), the John and Fannie Hertz Foundation (predoctoral fellowship to D. C. B.), Novartis (predoctoral fellowship to J. L. S.), the Philanthropic Education Organization (Scholar Award to J. L. S.), and Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, and Caltech for their generous financial support. The authors thank Professor Karl Scheidt (Northwestern) for helpful early discussions.

Attached Files

Accepted Version - nihms837140.pdf

Supplemental Material - ejoc_201600223_sm_miscellaneous_information.pdf


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