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Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin

Naga Venkata Sastry Mudiganti UGent, Sven Claessens UGent, Habonimana Pascal and Norbert De Kimpe UGent (2008) JOURNAL OF ORGANIC CHEMISTRY. 73(10). p.3867-3874
abstract
An efficient synthesis of naturally occurring compounds isolated from Pentas longiflora, cis-3,4-dihydroxy3,4-dihydromollugin 2, and trans-3,4-dihydroxy-3,4-dihydromollugin 3 is described. The O-protected mollugins were dihydroxylated using OSO4 to achieve the corresponding cis-dihydroxy derivatives in excellent yield. The synthesis of trans-3,4-dihydroxy-3,4-dihydromollugin was achieved using Oxone in good yield. A mechanism for the formation of cis-3,4-dihydroxymollugin acetonide from the reaction of mollugin with Oxone is proposed.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
CONSTITUENTS, NAPHTHOHYDROQUINONES, ANTHRAQUINONES, MOLLUGIN, RUBIA-CORDIFOLIA, PENTAS-LONGIFLORA, ROOTS, NAPHTHOQUINONES, PYRANONAPHTHOQUINONE, PENTALONGIN
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
73
issue
10
pages
3867 - 3874
publisher
AMER CHEMICAL SOC
place of publication
WASHINGTON, DC, USA
Web of Science type
Article
Web of Science id
000255698500028
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.952 (2008)
JCR rank
7/55 (2008)
JCR quartile
1 (2008)
ISSN
0022-3263
DOI
10.1021/jo800312j
language
English
UGent publication?
yes
classification
A1
id
533695
handle
http://hdl.handle.net/1854/LU-533695
date created
2009-03-30 09:38:22
date last changed
2017-01-02 09:56:31
@article{533695,
  abstract     = {An efficient synthesis of naturally occurring compounds isolated from Pentas longiflora, cis-3,4-dihydroxy3,4-dihydromollugin 2, and trans-3,4-dihydroxy-3,4-dihydromollugin 3 is described. The O-protected mollugins were dihydroxylated using OSO4 to achieve the corresponding cis-dihydroxy derivatives in excellent yield. The synthesis of trans-3,4-dihydroxy-3,4-dihydromollugin was achieved using Oxone in good yield. A mechanism for the formation of cis-3,4-dihydroxymollugin acetonide from the reaction of mollugin with Oxone is proposed.},
  author       = {Mudiganti, Naga Venkata Sastry and Claessens, Sven and Pascal, Habonimana and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {CONSTITUENTS,NAPHTHOHYDROQUINONES,ANTHRAQUINONES,MOLLUGIN,RUBIA-CORDIFOLIA,PENTAS-LONGIFLORA,ROOTS,NAPHTHOQUINONES,PYRANONAPHTHOQUINONE,PENTALONGIN},
  language     = {eng},
  number       = {10},
  pages        = {3867--3874},
  publisher    = {AMER CHEMICAL SOC},
  title        = {Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin},
  url          = {http://dx.doi.org/10.1021/jo800312j},
  volume       = {73},
  year         = {2008},
}

Chicago
Mudiganti, Naga Venkata Sastry, Sven Claessens, Habonimana Pascal, and Norbert De Kimpe. 2008. “Efficient Synthesis of Cis- and Trans-3,4-dihydroxy-3,4-dihydromollugin.” Journal of Organic Chemistry 73 (10): 3867–3874.
APA
Mudiganti, N. V. S., Claessens, S., Pascal, H., & De Kimpe, N. (2008). Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin. JOURNAL OF ORGANIC CHEMISTRY, 73(10), 3867–3874.
Vancouver
1.
Mudiganti NVS, Claessens S, Pascal H, De Kimpe N. Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin. JOURNAL OF ORGANIC CHEMISTRY. WASHINGTON, DC, USA: AMER CHEMICAL SOC; 2008;73(10):3867–74.
MLA
Mudiganti, Naga Venkata Sastry, Sven Claessens, Habonimana Pascal, et al. “Efficient Synthesis of Cis- and Trans-3,4-dihydroxy-3,4-dihydromollugin.” JOURNAL OF ORGANIC CHEMISTRY 73.10 (2008): 3867–3874. Print.