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Published May 19, 2014 | Accepted Version
Journal Article Open

Biosynthesis and Chemical Synthesis of Presilphiperfolanol Natural Products


Presilphiperfolanols constitute a family of biosynthetically important sesquiterpenes which can rearrange to diverse sesquiterpenoid skeletons. While the origin of these natural products can be traced to simple linear terpene precursors, the details of the enzymatic cyclization mechanism that forms the stereochemically dense tricyclic skeleton has required extensive biochemical, computational, and synthetic investigation. Parallel efforts to prepare the unique and intriguing structures of these compounds by total synthesis have also inspired novel strategies, thus resulting in four synthetic approaches and two completed syntheses. While the biosynthesis and chemical synthesis studies performed to date have provided much insight into the role and properties of these molecules, emerging questions regarding the biosynthesis of newer members of the family and subtle details of rearrangement mechanisms have yet to be explored.

Additional Information

© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Article first published online: 25 April 2014; Manuscript Received: 31 October 2013. We thank Dr. Scott Virgil, Prof. Sarah Reisman, Dr. Douglas Behenna, Dr. Mike Krout, Dr. Thomas Jensen, Dr. Phil Kun- Liang Wu, Dr. Alex Marziale, Dr. Jimin Kim, Douglas Duquette, Nick O'Connor, Jeffrey Holder, Nathan Bennett, and the reviewers for helpful discussions and suggestions. We thank NIH-NIGMS (R01GM080269), Roche, Abbott Laboratories, Amgen, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for awards and financial support

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