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Lyngbouilloside and the related macrolides lyngbyaloside, lyngbyaloside B and lyngbyaloside C have attracted a lot of attention over the past decade due to their intriguing architecture, their natural scarcity and their potential biological activities. This review aims to showcase the various strategies that have been used to access these natural products.
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Lyngbouilloside and related macrolides from marine cyanobacteria.
Nat Prod Commun
July 2013
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Lyngbouilloside and the related macrolides lyngbyaloside, lyngbyaloside B and lyngbyaloside C have attracted a lot of attention over the past decade due to their intriguing architecture, their natural scarcity and their potential biological activities. This review aims to showcase the various strategies that have been used to access these natural products.
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Org Lett
April 2013
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation.
View Article and Find Full Text PDFTotal synthesis of nominal lyngbouilloside aglycon.
Org Lett
January 2012
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
The first enantioselective total synthesis of the originally assigned structure of lyngbouilloside aglycon has been achieved using a particularly flexible route featuring an acylketene macrolactonization of a tertiary methyl carbinol as the key step. Comparison of the C13 chemical shifts of our synthetic aglycon with the ones pertaining to natural lyngbouilloside and lyngbyaloside C resulted in a possible stereochemical reassignment of the C11 stereogenic center.
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Org Lett
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University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1EW.
[reaction: see text] The conjugate addition of dithiols to bis-ynones generates a versatile masked 1,3,5-triketone platform. These functional units are useful intermediates for the synthesis of oxygen-containing heterocycles commonly found in polyketide natural products. The tetrahydropyranyl fragments of the marine macrolides Lyngbouilloside and Callipeltoside A have been synthesized with use of this methodology.
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J Nat Prod
June 2002
College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
A glycosidic macrolide, lyngbouilloside (1), was characterized from the marine cyanobacterium Lyngbya bouillonii collected from Papua New Guinea. Its structure was elucidated by spectroscopic analysis and chemical derivatization. Relative stereochemistry was deduced from homonuclear and heteronuclear coupling constants as well as NOE information.
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