Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

Michael T. Flavin; John D. Rizzo; Albert Khilevich; Alla Kucherenko; Abram K. Sheinkman; Vilayphone Vilaychack; Lin Lin; Wei Chen; Eugenia Mata Greenwood; Thitima Pengsuparp; John M. Pezzuto; Stephen H. Hughes; Thomas M. Flavin; Michael Cibulski; William A. Boulanger; Robert L. Shone; Ze Qi Xu

doi:10.1021/jm950797i

Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

Michael T. Flavin, John D. Rizzo, Albert Khilevich, Alla Kucherenko, Abram K. Sheinkman, Vilayphone Vilaychack, Lin Lin, Wei Chen, Eugenia Mata Greenwood, Thitima Pengsuparp, John M. Pezzuto, Stephen H. Hughes, Thomas M. Flavin, Michael Cibulski, William A. Boulanger, Robert L. Shone, Ze Qi Xu

Research output: Contribution to journal › Review article › peer-review

Original language	English
Pages (from-to)	1303-1313
Number of pages	11
Journal	Journal of Medicinal Chemistry
Volume	39
Issue number	6
DOIs	https://doi.org/10.1021/jm950797i
State	Published - Mar 15 1996
Externally published	Yes

ASJC Scopus Subject Areas

Molecular Medicine
Drug Discovery

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Flavin, M. T., Rizzo, J. D., Khilevich, A., Kucherenko, A., Sheinkman, A. K., Vilaychack, V., Lin, L., Chen, W., Greenwood, E. M., Pengsuparp, T., Pezzuto, J. M., Hughes, S. H., Flavin, T. M., Cibulski, M., Boulanger, W. A., Shone, R. L., & Xu, Z. Q. (1996). Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers. Journal of Medicinal Chemistry, 39(6), 1303-1313. https://doi.org/10.1021/jm950797i

Flavin, MT, Rizzo, JD, Khilevich, A, Kucherenko, A, Sheinkman, AK, Vilaychack, V, Lin, L, Chen, W, Greenwood, EM, Pengsuparp, T, Pezzuto, JM, Hughes, SH, Flavin, TM, Cibulski, M, Boulanger, WA, Shone, RL & Xu, ZQ 1996, 'Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers', Journal of Medicinal Chemistry, vol. 39, no. 6, pp. 1303-1313. https://doi.org/10.1021/jm950797i

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title = "Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers",

author = "Flavin, {Michael T.} and Rizzo, {John D.} and Albert Khilevich and Alla Kucherenko and Sheinkman, {Abram K.} and Vilayphone Vilaychack and Lin Lin and Wei Chen and Greenwood, {Eugenia Mata} and Thitima Pengsuparp and Pezzuto, {John M.} and Hughes, {Stephen H.} and Flavin, {Thomas M.} and Michael Cibulski and Boulanger, {William A.} and Shone, {Robert L.} and Xu, {Ze Qi}",

note = "The anti-HIV agent (±)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol [→ 5 → 6 → 11 → 18 → (±)-1], which includes Pechmann reaction, Friedel−Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction.",

year = "1996",

month = mar,

day = "15",

doi = "10.1021/jm950797i",

language = "English",

volume = "39",

pages = "1303--1313",

journal = "Journal of Medicinal Chemistry",

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TY - JOUR

T1 - Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

AU - Flavin, Michael T.

AU - Rizzo, John D.

AU - Khilevich, Albert

AU - Kucherenko, Alla

AU - Sheinkman, Abram K.

AU - Vilaychack, Vilayphone

AU - Lin, Lin

AU - Chen, Wei

AU - Greenwood, Eugenia Mata

AU - Pengsuparp, Thitima

AU - Pezzuto, John M.

AU - Hughes, Stephen H.

AU - Flavin, Thomas M.

AU - Cibulski, Michael

AU - Boulanger, William A.

AU - Shone, Robert L.

AU - Xu, Ze Qi

N1 - The anti-HIV agent (±)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol [→ 5 → 6 → 11 → 18 → (±)-1], which includes Pechmann reaction, Friedel−Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction.

PY - 1996/3/15

Y1 - 1996/3/15

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UR - http://www.scopus.com/inward/citedby.url?scp=13344277278&partnerID=8YFLogxK

U2 - 10.1021/jm950797i

DO - 10.1021/jm950797i

M3 - Review article

SN - 0022-2623

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SP - 1303

EP - 1313

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 6

ER -

Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

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