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Published May 30, 2002 | Supplemental Material
Journal Article Open

Progress toward the Synthesis of Garsubellin A and Related Phloroglucins: The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core


A highly diastereoselective single-step cyclization reaction provides access to the bicyclo[3.3.1]nonane core of the polyprenylated phloroglucin natural product garsubellin A. Further elaboration to a more functionalized analogue involves a sequential Claisen rearrangement/Grubbs olefin cross-metathesis strategy. Additionally, this strategy was extended to the preparation of the bis-quaternary carbon array found at the bridgehead positions of the phloroglucin natural products.

Additional Information

© 2002 American Chemical Society. Received April 3, 2002. Publication Date (Web): May 4, 2002. The authors are grateful to the California Institute of Technology, the Camille and Henry Dreyfus Foundation (New Faculty Award to B.M.S.), Merck Research Laboratories, and Pharmacia (graduate fellowship to S.J.S.) for generous financial support. The Grubbs, MacMillan, and Hsieh-Wilson labs are acknowledged for helpful discussions and the use of chemicals and instrumentation. We thank Larry Henling and Michael Day for solving the X-ray crystal structure and John Greaves (UCI) for obtaining high-resolution mass spectra. The authors would also like to acknowledge Professors Gary Spessard and Gretchen Hofmeister for helpful discussions and advice.

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