Total synthesis of brazilin

Youngeun Jung, Ikyon Kim

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.

Original languageEnglish
Pages (from-to)2001-2005
Number of pages5
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6

Fingerprint

Alkynes
Cyclization
Aldehydes
Ether
Modulation
Oxidation
Acids
brazilin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Jung, Youngeun ; Kim, Ikyon. / Total synthesis of brazilin. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 3. pp. 2001-2005.
@article{b43cd42476e746f085434715d3c8c782,
title = "Total synthesis of brazilin",
abstract = "Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70{\%} overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.",
author = "Youngeun Jung and Ikyon Kim",
year = "2015",
month = "2",
day = "6",
doi = "10.1021/jo502745j",
language = "English",
volume = "80",
pages = "2001--2005",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "3",

}

Total synthesis of brazilin. / Jung, Youngeun; Kim, Ikyon.

In: Journal of Organic Chemistry, Vol. 80, No. 3, 06.02.2015, p. 2001-2005.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Total synthesis of brazilin

AU - Jung, Youngeun

AU - Kim, Ikyon

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.

AB - Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.

UR - http://www.scopus.com/inward/record.url?scp=84922702440&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84922702440&partnerID=8YFLogxK

U2 - 10.1021/jo502745j

DO - 10.1021/jo502745j

M3 - Article

VL - 80

SP - 2001

EP - 2005

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -