Coibacins A and B: total synthesis and stereochemical revision

The Journal of Organic Chemistry
Vânia M T CarneiroRonaldo A Pilli

Abstract

The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.

References

Dec 1, 1983·The Journal of Antibiotics·S S StampwalaJ C French
Oct 1, 1982·Analytical Biochemistry·L C GreenS R Tannenbaum
Jun 19, 2001·Organic Letters·A B Smith, B M Brandt
Jul 18, 2001·Journal of the American Chemical Society·D L BogerW Zhong
Oct 25, 2001·Journal of the American Chemical Society·P Liu, E N Jacobsen
Oct 9, 2002·Current Medicinal Chemistry·D S LewyD L Boger
Jul 10, 2003·Angewandte Chemie·Ivan R Corrêa Júnior, Ronaldo A Pilli
Mar 23, 2005·Bioorganic & Medicinal Chemistry·Angelo de FátimaRonaldo Aloise Pilli
Oct 6, 2005·Bioorganic & Medicinal Chemistry·Angelo de FátimaRonaldo A Pilli
May 24, 2006·Chemical Communications : Chem Comm·David J PhillipsAndrew E Graham
Aug 15, 2008·Organic Letters·Robert J Bahde, Scott D Rychnovsky
Jun 6, 2009·Nature·Liangcai GuDavid H Sherman
Aug 21, 2009·Natural Product Reports·Martin E Maier
Aug 24, 2010·Bioorganic & Medicinal Chemistry·Débora Barbosa Vendramini-CostaJoão Ernesto de Carvalho
Jan 21, 2011·Organic Letters·Brendan D Kelly, Tristan H Lambert
Apr 28, 2012·Bioorganic & Medicinal Chemistry·Rosimeire Coura BarcelosRonaldo Aloise Pilli

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Citations

Feb 4, 2016·Natural Product Reports·John W BluntMichèle R Prinsep
Aug 28, 2015·Archives of Pharmacal Research·Hye-Dong YooMin-Sun Kim
Dec 25, 2019·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Roberta TetaAlfonso Mangoni
May 1, 2021·Marine Drugs·Shaden A M KhalifaHesham R El-Seedi
Feb 22, 2018·The Journal of Organic Chemistry·Alexander H ClevelandRendy Kartika

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