Synthesis of Several Cleistrioside and Cleistetroside Natural Products Via a Divergent De Novo Asymmetric Approach

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2010 Nov 3

PMID 21038879

Citations 11

Authors

Bulan Wu

Miaosheng Li

George A ODoherty

Affiliations

Soon will be listed here.

Abstract

The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19-24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation.

Citing Articles

asymmetric Achmatowicz approach to oligosaccharide natural products.

Kim S, Oiler J, Xing Y, ODoherty G Chem Commun (Camb). 2022; 58(93):12913-12926.

PMID: 36321854 PMC: 9710213. DOI: 10.1039/d2cc05280f.

Synthetic efforts on the road to marine natural products bearing 4--2,3,4,6-tetrasubstituted THPs: an update.

Farina-Ramos M, Garcia C, Martin V, Alvarez-Mendez S RSC Adv. 2022; 11(10):5832-5858.

PMID: 35423108 PMC: 8694735. DOI: 10.1039/d0ra10755g.

Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.

Blaszczyk S, Homan T, Tang W Carbohydr Res. 2018; 471:64-77.

PMID: 30508658 PMC: 6743478. DOI: 10.1016/j.carres.2018.11.012.

Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Ghosh A, Brindisi M RSC Adv. 2017; 6(112):111564-111598.

PMID: 28944049 PMC: 5603243. DOI: 10.1039/C6RA22611F.

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.

Gomez A, Lobo F, Miranda S, Lopez J Molecules. 2015; 20(5):8357-94.

PMID: 26007170 PMC: 6272535. DOI: 10.3390/molecules20058357.

References

Guo H, ODoherty G . de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation. Org Lett. 2005; 7(18):3921-4. DOI: 10.1021/ol051383e. View

Guo H, ODoherty G . De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction. Angew Chem Int Ed Engl. 2007; 46(27):5206-8. DOI: 10.1002/anie.200701354. View

Clausen M, Madsen R . Synthesis of hexasaccharide fragments of pectin. Chemistry. 2003; 9(16):3821-32. DOI: 10.1002/chem.200204636. View

Seidel V, Bailleul F, Waterman P . Novel oligorhamnosides from the stem bark of Cleistopholis glauca. J Nat Prod. 2000; 63(1):6-11. DOI: 10.1021/np9901478. View

Hu J, Garo E, Hough G, Goering M, ONeil-Johnson M, Eldridge G . Antibacterial, partially acetylated oligorhamnosides from Cleistopholis patens. J Nat Prod. 2006; 69(4):585-90. DOI: 10.1021/np050438i. View

Cheng L, Chen Q, Du Y . Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens. Carbohydr Res. 2007; 342(11):1496-501. DOI: 10.1016/j.carres.2007.05.019. View

Babu R, ODoherty G . A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. J Am Chem Soc. 2003; 125(41):12406-7. DOI: 10.1021/ja037097k. View

Glen A, Leigh D, Martin R, Smart J, Truscello A . The regioselective tert-butyldimethylsilylation of the 6'-hydroxyl group of lactose derivatives via their dibutylstannylene acetals. Carbohydr Res. 1993; 248:365-9. DOI: 10.1016/0008-6215(93)84143-t. View

Shan M, Xing Y, ODoherty G . De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners. J Org Chem. 2010; 74(16):5961-6. DOI: 10.1021/jo9009722. View

10.

Seidel V, Bailleul F, Waterman P . Partially acetylated tri- and tetrarhamnoside dodecanyl ether derivatives from Cleistopholis patens. Phytochemistry. 1999; 52(3):465-72. DOI: 10.1016/s0031-9422(99)00224-1. View

11.

Babu R, Zhou M, ODoherty G . De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction. J Am Chem Soc. 2004; 126(11):3428-9. DOI: 10.1021/ja039400n. View

12.

Guo H, ODoherty G . De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide. J Org Chem. 2008; 73(14):5211-20. DOI: 10.1021/jo800691v. View

13.

Harris J, Keranen M, Nguyen H, Young V, ODoherty G . Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions. Carbohydr Res. 2000; 328(1):17-36. DOI: 10.1016/s0008-6215(00)00031-8. View

14.

Cui B, Chai H, Santisuk T, Reutrakul V, Farnsworth N, Cordell G . Novel cytotoxic acylated oligorhamnosides from Mezzettia leptopoda. J Nat Prod. 1998; 61(12):1535-8. DOI: 10.1021/np980270j. View

15.

Fernandez P, Jimenez-Barbero J . Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl beta-lactoside as ligands for the Ricinus communis lectins. Carbohydr Res. 1994; 254:61-79. DOI: 10.1016/0008-6215(94)84243-4. View

16.

Shan M, ODoherty G . Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations. Org Lett. 2010; 12(13):2986-9. PMC: 2892554. DOI: 10.1021/ol101009q. View

17.

Zhang Z, Wang P, Ding N, Song G, Li Y . Total synthesis of cleistetroside-2, partially acetylated dodecanyl tetrarhamnoside derivative isolated from Cleistopholis patens and Cleistopholis glauca. Carbohydr Res. 2007; 342(9):1159-68. DOI: 10.1016/j.carres.2007.03.014. View

18.

Shan M, ODoherty G . De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation. Org Lett. 2006; 8(22):5149-52. PMC: 2529254. DOI: 10.1021/ol062076r. View

19.

Harris J, Keranen M, ODoherty G . Syntheses of D- and L-Mannose, Gulose, and Talose via Diastereoselective and Enantioselective Dihydroxylation Reactions. J Org Chem. 2001; 64(9):2982-2983. DOI: 10.1021/jo990410+. View

20.

Lowary T, Hindsgaul O . Recognition of synthetic O-methyl, epimeric, and amino analogues of the acceptor alpha-L-Fuc p-(1-->2)-beta-D-Gal p-OR by the blood-group A and B gene-specified glycosyltransferases. Carbohydr Res. 1994; 251:33-67. DOI: 10.1016/0008-6215(94)84275-2. View