Total synthesis of Michellamines A-C: Important anti-HIV agents

Thomas R. Hoye; Minzhang Chen; Liang Mi; Owen P. Priest

doi:10.1016/S0040-4039(00)78487-5

Total synthesis of Michellamines A-C: Important anti-HIV agents

Thomas R. Hoye^*, Minzhang Chen, Liang Mi, Owen P. Priest

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2′-binaphthol.

Original language	English (US)
Pages (from-to)	8747-8750
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(00)78487-5
State	Published - Nov 21 1994

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)78487-5

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title = "Total synthesis of Michellamines A-C: Important anti-HIV agents",

abstract = "Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2′-binaphthol.",

author = "Hoye, {Thomas R.} and Minzhang Chen and Liang Mi and Priest, {Owen P.}",

note = "Funding Information: Acknowledgments This work was supported by grant #CA-M284 awarded by the DHHS. A sample of natural michellamine B was kindly provided by Dr. Ven L. Narayanan of the Drug Synthesis & Chemistry Branch, Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

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doi = "10.1016/S0040-4039(00)78487-5",

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T2 - Important anti-HIV agents

AU - Hoye, Thomas R.

AU - Chen, Minzhang

AU - Mi, Liang

AU - Priest, Owen P.

N1 - Funding Information: Acknowledgments This work was supported by grant #CA-M284 awarded by the DHHS. A sample of natural michellamine B was kindly provided by Dr. Ven L. Narayanan of the Drug Synthesis & Chemistry Branch, Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 1994/11/21

Y1 - 1994/11/21

N2 - Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2′-binaphthol.

AB - Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2′-binaphthol.

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Total synthesis of Michellamines A-C: Important anti-HIV agents

Abstract

ASJC Scopus subject areas

UN SDGs

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