The Library
A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones
Tools
Clarke, Paul A., Sellars, Philip B. and Nasir, Nadiah Mad (2015) A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones. Organic & Biomolecular Chemistry, 13 (16). pp. 4743-4750. doi:10.1039/c5ob00292c ISSN 1477-0520.
|
PDF
WRAP_1570084-wmg-120416-a_maitland-japp_inspired_synthesis_of_dihyropyran-4-ones_and_their_stereoselective_conversion_to_functionalised_tetrahydropyran-4-ones_org._biomol._chem._2015_13_4743.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (619Kb) | Preview |
Official URL: http://dx.doi.org/10.1039/C5OB00292C
Abstract
The Maitland–Japp reaction has been extended to the synthesis of highly functionalised dihydropyran-4-ones. These dihydropyran-4-ones can in turn be converted stereoselectively into tetrahydropyran-4-ones with tertiary and quaternary stereocentres via the one-pot addition of hydride or carbon nucleophiles and trapping with carbon electrophiles. The utility of this method is demonstrated by providing access to the functionalised tetrahydropyran units present in a component of the Civet fragrance and the anticancer polyketide lasonolide A.
Item Type: | Journal Article | ||||||||
---|---|---|---|---|---|---|---|---|---|
Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Engineering > WMG (Formerly the Warwick Manufacturing Group) | ||||||||
Library of Congress Subject Headings (LCSH): | Chemistry, Organic | ||||||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||||||
Publisher: | Royal Society of Chemistry | ||||||||
ISSN: | 1477-0520 | ||||||||
Official Date: | 12 March 2015 | ||||||||
Dates: |
|
||||||||
Volume: | 13 | ||||||||
Number: | 16 | ||||||||
Page Range: | pp. 4743-4750 | ||||||||
DOI: | 10.1039/c5ob00292c | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 22 April 2016 | ||||||||
Date of first compliant Open Access: | 22 April 2016 | ||||||||
Funder: | Ministry of Higher Education (Malaysia), University of York |
Request changes or add full text files to a record
Repository staff actions (login required)
View Item |
Downloads
Downloads per month over past year