Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

Kyung Hee Kim; Cheol Hong Cheon

doi:10.1039/c7qo00195a

Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

Kyung Hee Kim, Cheol Hong Cheon

Department of Chemistry

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

5 Citations (Scopus)

Abstract

Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler-Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.

Original language	English
Pages (from-to)	1341-1349
Number of pages	9
Journal	Organic Chemistry Frontiers
Volume	4
Issue number	7
DOIs	https://doi.org/10.1039/c7qo00195a
Publication status	Published - 2017 Jul

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1039/c7qo00195a

Cite this

@article{cac8a5d8389f43aea9c157333aa70012,

title = "Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer",

abstract = "Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler-Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.",

author = "Kim, {Kyung Hee} and Cheon, {Cheol Hong}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-20100020209 and NRF-2015R1D1A1A01057200). C.-H. C. also acknowledges financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis)",

year = "2017",

month = jul,

doi = "10.1039/c7qo00195a",

language = "English",

volume = "4",

pages = "1341--1349",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

AU - Kim, Kyung Hee

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-20100020209 and NRF-2015R1D1A1A01057200). C.-H. C. also acknowledges financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis)

PY - 2017/7

Y1 - 2017/7

N2 - Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler-Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.

AB - Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler-Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.

UR - http://www.scopus.com/inward/record.url?scp=85021768109&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85021768109&partnerID=8YFLogxK

U2 - 10.1039/c7qo00195a

DO - 10.1039/c7qo00195a

M3 - Article

AN - SCOPUS:85021768109

SN - 2052-4110

VL - 4

SP - 1341

EP - 1349

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 7

ER -

Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this