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

(2008) JOURNAL OF ORGANIC CHEMISTRY. 73(10). p.3867-3874
Author
Organization
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.
Keywords
CONSTITUENTS, NAPHTHOHYDROQUINONES, ANTHRAQUINONES, MOLLUGIN, RUBIA-CORDIFOLIA, PENTAS-LONGIFLORA, ROOTS, NAPHTHOQUINONES, PYRANONAPHTHOQUINONE, PENTALONGIN

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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.
@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},
}

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