Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene

A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and co...

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Published in:Journal of the American Chemical Society 2017-11, Vol.139 (44), p.15656-15659
Main Authors: Hernandez, Lucas W, Pospech, Jola, Klöckner, Ulrich, Bingham, Tanner W, Sarlah, David
Format: Article
Language:English
Subjects:
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
benzene
Benzene - chemical synthesis
Benzene - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chemistry Techniques, Synthetic - methods
enantioselectivity
Hydroxylation
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a516t-23d7362ccfaaaa6ffdbffeb1550b609f1e851b7080cab7c15dbf4d3a6c961b083
cites cdi_FETCH-LOGICAL-a516t-23d7362ccfaaaa6ffdbffeb1550b609f1e851b7080cab7c15dbf4d3a6c961b083
container_end_page 15659
container_issue 44
container_start_page 15656
container_title Journal of the American Chemical Society
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creator Hernandez, Lucas W
Pospech, Jola
Klöckner, Ulrich
Bingham, Tanner W
Sarlah, David
description A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.
doi_str_mv 10.1021/jacs.7b10351
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subjects Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
benzene
Benzene - chemical synthesis
Benzene - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chemistry Techniques, Synthetic - methods
enantioselectivity
Hydroxylation
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Stereoisomerism
title Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene
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