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Progress toward the total synthesis of psiguadial B

Chapman, Lauren M. and Reisman, Sarah E. (2015) Progress toward the total synthesis of psiguadial B. In: 250th American Chemical Society National Meeting & Exposition, August 16-20, 2015, Boston, MA.

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Progress toward the total synthesis of psiguadial B, a diformyl phloroglucinol meroterpenoid natural product, is disclosed. The synthetic strategy employed has resulted in the development of three key transformations: a photochem. Wolff rearrangement with tandem asym. ketene addn., a palladium-catalyzed C(sp )-H activation reaction of a cyclobutane substrate, and an inverse-electron demand hetero-Diels Alder cycloaddn. between a highly-oxidized ortho-quinone methide and a cyclohexanone-derived enol ether. This strategy enables rapid assembly of the tricylic core of psiguadial B, with de novo construction of the transfused cyclobutane ring found in several natural products in this family. Current efforts directed toward developing a successful cyclization reaction to form a highly strained seven-membered ring will also be presented.

Item Type:Conference or Workshop Item (Paper)
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Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2015 American Chemical Society.
Record Number:CaltechAUTHORS:20150916-130810447
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60282
Deposited By: Tony Diaz
Deposited On:16 Sep 2015 21:33
Last Modified:03 Oct 2019 08:55

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