Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

Bioorganic & Medicinal Chemistry Letters
K N JayaprakashBert Fraser-Reid

Abstract

Regioselective mannosylations of a myoinositol acceptor diol are readily achieved by Lewis acid mediated iodinolysis of n-pentenyl ortho-esters. The procedure affords a psuedotrisaccharide to which the phosphoglyceryl and other lipid residues are added leading to the key biosynthetic intermediate of Mycobacterium species.

References

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Citations

Sep 23, 2011·Journal of Medicinal Chemistry·Gary D AingeGavin F Painter
Aug 1, 2012·The Journal of Organic Chemistry·Gregory M RankinDavid S Larsen
May 13, 2005·Organic & Biomolecular Chemistry·Jacinta A Watt, Spencer J Williams
Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt
Dec 24, 2008·Chemistry : a European Journal·Pratap S Patil, Shang-Cheng Hung
Sep 20, 2006·The Journal of Immunology : Official Journal of the American Association of Immunologists·Dirk M ZajoncIan A Wilson
Dec 4, 2008·Journal of the American Chemical Society·Siwarutt BoonyarattanakalinPeter H Seeberger
Nov 8, 2008·The Journal of Organic Chemistry·Bert Fraser-ReidChangalvala V S Ramamurty
Jun 28, 2007·The Journal of Organic Chemistry·K N JayaprakashBert Fraser-Reid
Mar 16, 2006·Journal of the American Chemical Society·Xinyu LiuPeter H Seeberger

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