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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. / Evans, Amanda C.; Longbottom, Deborah A.; Matsuoka, Masato et al.
In: Organic and Biomolecular Chemistry , Vol. 7, No. 4, 2009, p. 747-760.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Evans, AC, Longbottom, DA, Matsuoka, M, Davies, JE, Turner, R, Franckevicius, V & Ley, SV 2009, 'Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis', Organic and Biomolecular Chemistry , vol. 7, no. 4, pp. 747-760. https://doi.org/10.1039/b813494d

APA

Evans, A. C., Longbottom, D. A., Matsuoka, M., Davies, J. E., Turner, R., Franckevicius, V., & Ley, S. V. (2009). Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. Organic and Biomolecular Chemistry , 7(4), 747-760. https://doi.org/10.1039/b813494d

Vancouver

Evans AC, Longbottom DA, Matsuoka M, Davies JE, Turner R, Franckevicius V et al. Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. Organic and Biomolecular Chemistry . 2009;7(4):747-760. doi: 10.1039/b813494d

Author

Evans, Amanda C. ; Longbottom, Deborah A. ; Matsuoka, Masato et al. / Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. In: Organic and Biomolecular Chemistry . 2009 ; Vol. 7, No. 4. pp. 747-760.

Bibtex

@article{59d88fb3f1ac4c77ae09f01587c30f84,
title = "Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis",
abstract = "A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.",
keywords = "PROCHIRAL ANHYDRIDES, BENZOPYRANO-ISOXAZOLIDINE AUXILIARY, SUCCINIC ANHYDRIDES, ASYMMETRIC-SYNTHESIS, CHIRAL AUXILIARIES, DICARBOXYLIC ANHYDRIDES, MAMMALIAN TARGET, MODIFIED CINCHONA ALKALOIDS, ISOPROPYL HEMIESTERS, ENANTIOSELECTIVE SYNTHESIS",
author = "Evans, {Amanda C.} and Longbottom, {Deborah A.} and Masato Matsuoka and Davies, {John E.} and Richard Turner and Vilius Franckevicius and Ley, {Steven V.}",
year = "2009",
doi = "10.1039/b813494d",
language = "English",
volume = "7",
pages = "747--760",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "4",

}

RIS

TY - JOUR

T1 - Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

AU - Evans, Amanda C.

AU - Longbottom, Deborah A.

AU - Matsuoka, Masato

AU - Davies, John E.

AU - Turner, Richard

AU - Franckevicius, Vilius

AU - Ley, Steven V.

PY - 2009

Y1 - 2009

N2 - A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

AB - A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

KW - PROCHIRAL ANHYDRIDES

KW - BENZOPYRANO-ISOXAZOLIDINE AUXILIARY

KW - SUCCINIC ANHYDRIDES

KW - ASYMMETRIC-SYNTHESIS

KW - CHIRAL AUXILIARIES

KW - DICARBOXYLIC ANHYDRIDES

KW - MAMMALIAN TARGET

KW - MODIFIED CINCHONA ALKALOIDS

KW - ISOPROPYL HEMIESTERS

KW - ENANTIOSELECTIVE SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=59849089652&partnerID=8YFLogxK

U2 - 10.1039/b813494d

DO - 10.1039/b813494d

M3 - Journal article

VL - 7

SP - 747

EP - 760

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 4

ER -