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https://hdl.handle.net/2440/122436
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Type: | Journal article |
Title: | ortho-Quinone methide cyclizations inspired by the busseihydroquinone family of natural products |
Author: | Burchill, L. Pepper, H.P. Sumby, C.J. George, J.H. |
Citation: | Organic Letters, 2019; 21(20):8304-8307 |
Publisher: | American Chemical Society |
Issue Date: | 2019 |
ISSN: | 1523-7060 1523-7052 |
Statement of Responsibility: | Laura Burchill, Henry P. Pepper, Christopher J. Sumby, and Jonathan H. George |
Abstract: | A series of cascade reactions of o-quinone methides have been developed based on the proposed biosynthesis of busseihydroquinone and parvinaphthol meroterpenoid natural products. The polycyclic framework of the most complex family members, busseihydroquinone E and parvinaphthol C, was assembled by an intramolecular [4 + 2] cycloaddition of an electron-rich chromene substrate. The resultant cyclic enol ether underwent rearrangements under acidic or oxidative conditions, which led to a new total synthesis of rhodonoid D. |
Keywords: | Indolequinones Biological Products Molecular Structure Cyclization Stereoisomerism |
Rights: | © 2019 American Chemical Society |
DOI: | 10.1021/acs.orglett.9b03060 |
Grant ID: | http://purl.org/au-research/grants/arc/FT170100437 |
Published version: | http://dx.doi.org/10.1021/acs.orglett.9b03060 |
Appears in Collections: | Aurora harvest 8 Chemistry publications |
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