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Biosynthesis and Chemical Synthesis of Presilphiperfolanol Natural Products

Hong, Allen Y. and Stoltz, Brian M. (2014) Biosynthesis and Chemical Synthesis of Presilphiperfolanol Natural Products. Angewandte Chemie International Edition, 53 (21). pp. 5248-5260. ISSN 1433-7851. PMCID PMC4334158. http://resolver.caltech.edu/CaltechAUTHORS:20140505-091759313

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201309494DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201309494/abstractPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334158/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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
Funders:
Funding AgencyGrant Number
NIHR01 GM080269
RocheUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:biosynthesis; natural products; structure elucidation; terpenoids; total synthesis
PubMed Central ID:PMC4334158
Record Number:CaltechAUTHORS:20140505-091759313
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140505-091759313
Official Citation:Hong, A. Y. and Stoltz, B. M. (2014), Biosynthesis and Chemical Synthesis of Presilphiperfolanol Natural Products. Angew. Chem. Int. Ed., 53: 5248–5260. doi: 10.1002/anie.201309494
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:45479
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:05 May 2014 19:46
Last Modified:20 Jul 2017 23:57

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