A Concise Total Synthesis of (±)‐Vibralactone

Nistanaki, Sepand K. and Boralsky, Luke A. and Pan, Roy D. and Nelson, Hosea M. (2019) A Concise Total Synthesis of (±)‐Vibralactone. Angewandte Chemie International Edition, 58 (6). pp. 1724-1726. ISSN 1433-7851. PMCID PMC6351154. doi:10.1002/anie.201812711. https://resolver.caltech.edu/CaltechAUTHORS:20210811-225351791

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Abstract

Disclosed is a five-step synthesis of (±)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one produces both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone produces a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. This concise and modular route to the natural product provides the shortest total synthesis of (±)-vibralactone reported to date.

Item Type:

Article

Related URLs:

URL	URL Type	Description
https://doi.org/10.1002/anie.201812711	DOI	Article
https://www.ncbi.nlm.nih.gov/pmc/articles/pmc6351154/	PubMed Central	Article
https://doi.org/10.26434/chemrxiv.7245167.v2	DOI	Discussion Paper

ORCID:

Author	ORCID
Nistanaki, Sepand K.	0000-0002-5252-803X
Nelson, Hosea M.	0000-0002-4666-2793

Additional Information:

© 2019 Wiley-VCH. Issue Online: 29 January 2019. Version of Record online: 09 January 2019. Accepted manuscript online: 13 December 2018. Manuscript received: 05 November 2018. We thank the David and Lucile Packard Foundation (to H.M.N.) and the Alfred P. Sloan Foundation (to H.M.N.) for generous support. S.K.N. acknowledges the USPHS National Research Service Award (T32GM008496). L.A.B. acknowledges the USPHS National Research Service Award (5T32GM008496). We thank Dr. S. Khan and the UCLA Molecular Instrumentation Center for NMR instrumentation, X-ray crystallography (S. Khan), and mass spectrometry. This material is based upon work supported by the National Institutes of Health under instrumentation grant no. 1S10OD016387-01. We also thank the mass spectrometry facility at the University of California, Irvine for mass spectrometry data. We thank the group of M. A. Garcia-Garibay (UCLA) for the use of their Hanovia lamps during initial photochemical experiments. We thank N. K. Garg (UCLA) and P. G. Harran (UCLA) for useful discussions. The authors declare no conflict of interest.

Funders:

Funding Agency	Grant Number
David and Lucile Packard Foundation	UNSPECIFIED
Alfred P. Sloan Foundation	UNSPECIFIED
NIH Predoctoral Fellowship	T32GM008496
NIH	1S10OD016387-01

Subject Keywords:

cyclopropanation; housane; photochemistry; ring expansion; total synthesis

Issue or Number:

PubMed Central ID:

PMC6351154

DOI:

10.1002/anie.201812711

Record Number:

CaltechAUTHORS:20210811-225351791

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20210811-225351791

Official Citation:

S. K. Nistanaki, L. A. Boralsky, R. D. Pan, H. M. Nelson, Angew. Chem. Int. Ed. 2019, 58, 1724.

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No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

110216

Collection:

CaltechAUTHORS

Deposited By:

George Porter

Deposited On:

12 Aug 2021 19:15

Last Modified:

18 Aug 2021 18:47

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