Total synthesis of a stereoisomer of bistramide C and assignment of configuration of the natural product

Chemistry : a European Journal
P WipfSeiji Yoshimura

Abstract

After the isolation of the bioactive polyether bistramide C from the marine ascidian Lissoclinum bistratum in 1988, NMR spectroscopic investigations over the next 12 years reduced the total number of possible stereoisomers of this compound from 1024 to 32. Based on the preparation of segments of the natural product as well as the total synthesis of a randomly selected stereoisomer of bistramide C, the stereochemical puzzle could be further simplified to eight possible stereoisomers. A convergent three-segment coupling strategy, the use of a common, D-glucose-derived intermediate for the preparation of pyran rings in two segments, a stereoselective photo-spiroketalization, and the use of azides to minimize protective group manipulations before segment couplings are highlights of the synthetic approach. The total synthesis also provided the key segments for a chiroptical analysis according to van't Hoff's principle of optical superposition, which was crucial for the assignment of a sole relative and absolute configuration of the natural product. Bistramide C represents therefore the first member of this class of structurally unusual marine polyethers whose configuration is known as a result of the combined use of synthetic and ch...Continue Reading

References

Jun 1, 1989·Journal of Medicinal Chemistry·B M DegnanD J Watters
Jun 25, 1999·Biochemical and Biophysical Research Communications·W E JohnsonC M Bunce
May 18, 2000·The Journal of Organic Chemistry·P Wipf, Y Uto
Jan 11, 2001·Organic Letters·P Wipf, J L Methot
Sep 13, 2001·Journal of the American Chemical Society·K M SpechtD Kahne

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Citations

Apr 13, 2006·Journal of the American Chemical Society·Michael T Crimmins, Amy C DeBaillie
Sep 17, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·B Rama Raju, Anil K Saikia
Apr 9, 2016·Organic & Biomolecular Chemistry·Raghu Vannam, Mark W Peczuh
Aug 22, 2012·Angewandte Chemie·Pragna Pratic DasJin Kun Cha
Jun 7, 2008·Physical Chemistry Chemical Physics : PCCP·Nicholas J Russ, T Daniel Crawford
Jul 6, 2005·Chemical Communications : Chem Comm·Peter Wipf, Tamara D Hopkins
Sep 23, 2010·Chemistry & Biodiversity·Thorben NawrathStefan Schulz
Dec 22, 2009·Organic & Biomolecular Chemistry·Jonathan SperryMargaret A Brimble
Feb 16, 2010·Angewandte Chemie·Satya P ChintaStefan Schulz
Oct 9, 2007·Organic Letters·J S Yadav, Lakshindra Chetia
May 12, 2010·Journal of the American Chemical Society·Syed Alipayam RizviSergey A Kozmin
Aug 23, 2019·Journal of the American Chemical Society·Yong ChenNuno Maulide
Oct 19, 2011·Organic Letters·Malgorzata CommandeurJanine Cossy
May 22, 2018·The Journal of Organic Chemistry·Jessie H BirdBridget L Stocker
Nov 8, 2003·The Journal of Organic Chemistry·Peter Wipf, Thomas H Graham
Jan 16, 2007·Organic Letters·Jason T LoweJames S Panek
Aug 5, 2004·Journal of the American Chemical Society·Alexander V StatsukSergey A Kozmin

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