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Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland–Japp derived 2H-dihydropyran-4-ones : a total synthesis of diospongin B
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Clarke, Paul A., Nasir, Nadiah Mad, Sellars, Philip B., Peter, Alejandra M., Lawson, Connor A. and Burroughs, James L. (2016) Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland–Japp derived 2H-dihydropyran-4-ones : a total synthesis of diospongin B. Organic & Biomolecular Chemistry, 14 (28). pp. 6840-6852. doi:10.1039/c6ob01182a ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/C6OB01182A
Abstract
6-Substituted-2H-dihydropyran-4-one products of the Maitland–Japp reaction have been converted into tetrahydropyrans containing uncommon substitution patterns. Treatment of 6-substituted-2H-dihydropyran-4-ones with carbon nucleophiles led to the formation of tetrahydropyran rings with the 2,6-trans-stereochemical arrangement. Reaction of the same 6-substituted-2H-dihydropyran-4-ones with L-Selectride led to the formation of 3,6-disubstituted tetrahydropyran rings, while trapping of the intermediate enolate with carbon electrophiles in turn led to the formation 3,3,6-trisubstituted tetrahydropyran rings. The relative stereochemical configuration of the new substituents was controlled by the stereoelectronic preference for pseudo-axial addition of the nucleophile and trapping of the enolate from the opposite face. Application of these methods led to a synthesis of the potent anti-osteoporotic diarylheptanoid natural product diospongin B.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Library of Congress Subject Headings (LCSH): | Organic compounds -- Synthesis | ||||||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||||||
Publisher: | Royal Society of Chemistry | ||||||||
ISSN: | 1477-0520 | ||||||||
Official Date: | 20 June 2016 | ||||||||
Dates: |
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Volume: | 14 | ||||||||
Number: | 28 | ||||||||
Page Range: | pp. 6840-6852 | ||||||||
DOI: | 10.1039/c6ob01182a | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 15 July 2016 | ||||||||
Date of first compliant Open Access: | 15 July 2016 | ||||||||
Funder: | University of York, Malaysia. Kementerian Pendidikan , Erasmus Mundus (Program) |
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