- Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent
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An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Bronsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis
- Ghosh, Arun K.,Cheng, Xu
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supporting information; experimental part
p. 4108 - 4111
(2011/10/04)
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- First stereoselective synthesis of the C(1)-C(13) fragment of dolabelides using ruthenium-SYNPHOS-catalyzed asymmetric hydrogenation reactions
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The first stereocontrolled synthesis of the C(1)-C(13) fragment of cytotoxic macrolides dolabelides is reported. The C(3), C(7), C(9) and C(11) hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenation reactions of the adequate β-keto esters and β-hydroxy ketone. Georg Thieme Verlag Stuttgart.
- Le Roux, Rémi,Desroy, Nicolas,Phansavath, Phannarath,Genêt, Jean-Pierre
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p. 429 - 432
(2007/10/03)
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- Formal synthesis of (-)-apicularen A
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(Matrix Presented) A formal synthesis of (-)-apicularen A has been completed. The synthesis features a cyanohydrin acetonide coupling as a convergent approach to the C9-C18 segment and an intramolecular Diels-Alder addition sequence to create both the 10-membered macrocycle and the aromatic ring.
- Graetz, Benjamin R.,Rychnovsky, Scott D.
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p. 3357 - 3360
(2007/10/03)
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- Synthesis of the C1-C28 Portion of Spongistatin 1 (Altohyrtin A)
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A synthetic approach was developed to the C1-C28 subunit of spongistatin 1 (altohyrtin A, 65). The key step was the coupling of the AB and CD spiroketal moieties via an anti-aldol reaction of aldehyde 62 and ethyl ketone 57. The development of a method for the construction of the AB spiroketal fragment is described and included the desymmetrization of C2-symmetric diketone 10 and the differentiation of the two primary alcohols of 16. Further elaboration of this advanced intermediate to the desired aldehyde 62 included an Evans' syn-aldol reaction and Tebbe olefination. The synthesis of the CD spiroketal fragment 56 involved the ketalization of a triol-dione, generated in situ by deprotection of 45, to provide a favorable ratio (6-7:1) of spiroketal isomers 46 and 47, respectively. The overall protecting group strategy, involving many selective manipulations of silyl protecting groups, was successfully developed to provide the desired C1-C28 subunit of spongistatin 1 (altohyrtin A) (65).
- Claffey, Michelle M.,Hayes, Christopher J.,Heathcock, Clayton H.
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p. 8267 - 8274
(2007/10/03)
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- Enantioselective acyclic stereoselection under catalyst control - III. A very short asymmetric synthesis of the bryostatin C1-C9 segment using the chiral oxazaborolidinone-promoted aldol reaction
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A very short asymmetric synthesis of the bryostatin C1-C9 segment was achieved by three sequential chiral oxazaborolidinone-promoted aldol reactions under 'catalyst control'. This synthetic methodology is based on a direct asymmetric
- Kiyooka, Syun-Ichi,Maeda, Hirofumi
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p. 3371 - 3374
(2007/10/03)
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- Enantiospecific synthesis of optically pure (3S)-hydroxy esters by the stereocontrolled yeast reduction of α-sulfenyl-β-ketoesters
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Stereocontrol in Baker's yeast reduction of β-ketoesters was successfully achieved by introducing the sulfenyl group at the α-position of the esters to afford optically pure (S)-β-hydroxy esters.
- Fujisawa,Itoh,Sato
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p. 5083 - 5086
(2007/10/02)
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