88671-02-7Relevant articles and documents
Stereochemistry of enacyloxins. Part 5: Synthesis of a C9′-C15′ fragment of enacyloxins, a series of antibiotics from Frateuria sp. W-315
Furukawa, Hiroyuki,Hoshikawa, Hiroaki,Igarashi, Wataru,Yaosaka, Manabu,Yamada, Teiko,Kuwahara, Shigefumi,Kiyota, Hiromasa
, p. 3 - 5 (2011/10/08)
The C9′-C15′ fragment of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, was synthesized from diethyl D-tartrate. Copyright by Walter de Gruyter Berlin Boston.
Synthesis of brassinolide and its biosynthetic precursors using methyl 3-hydroxy-2-methylpropionate
Khripach,Zhabinskii,Parkhimovich,Gulyakevich
experimental part, p. 240 - 249 (2010/04/26)
Formal synthesis of plant hormones that belong to the group of 24α-methylbrassinosteroids, including brassinolide and its biosynthetic precursors with one hydroxyl group in their side chain, was performed. Stereochemistry of a methyl group at the C24 atom
A mild and versatile method for the tetrahydropyranylation of alcohols and their detetrahydropyranylation
Yadav,Srinivas, Dale,Reddy, Gondi Sudershan
, p. 1399 - 1404 (2007/10/03)
An efficient and mild method for tetrahydropyranylation of alcohols and their detetrahydropranylation using NH4Cl is described. This protocol provides a useful alternative tetrahydropyranylation of alcohols and their deprotection at different pH.
The synthesis of the C-9 to C-21 sector of discodermolide: An efficient route to the C13-14 Z-trisubstituted alkene
Yang, Ge,Myles, David C.
, p. 2503 - 2504 (2007/10/02)
The synthesis of the C-9 to C-21 sector of the immunosuppressive marine natural product discodermolide is described. The C-9 to C-15 subunit is synthesized in five steps from aldehyde 5 using the diene aldehyde cyclocondensation reaction. Diastereoselective alkylation of the previously synthesized C-16 to C-21 subunit by a suitably functionalized C-9 to C-15 synthon (3) leads to the C-9 to C-21 sector of discodermolide.
An Alkylative Strategy to the C-13 to C-21 Sector of Discodermolide
Yang, Ge,Myles, David C.
, p. 1313 - 1316 (2007/10/02)
An approach to the C-13 to C-21 sector if the immunosuppressive marine natural product discodermolide (1) is described.The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate.Either diastereomer of alkylation can be obtained by selecting the appropriate counter ion.The C-16 to C-21 subunit is prepared in two steps from 11.
Diastereofacial Selection in Nitrile Oxide Cycloaddition Reactions. The Anti-Directing Effect of an Allylic Oxygen and Some New Results on the Ring Metalation of Isoxazolines. A Synthesis of (+/-)-Blastmycinone
Kozikowski,, Alan P.,Ghosh, Arun K.
, p. 2762 - 2772 (2007/10/02)
The extent of diastereoselectivity associated with the reactions of nitrile oxides with alkenes bearing an allylic oxygen substituent has been studied.Reasonable levels of such diastereoselectivity have been found when the tert-butyldimethylsilyl ether derivative of 3-buten-2-ol (5) or (+)-(S)-isopropylidene-3-butene-1,2-diol (1) are employed as dipolarophiles.The stereochemical course of these cycloaddition reactions has been proven rigorously through the transformation of the adducts to known γ-lactones.The stereochemistry associated with the metalation/alkylation of 5-alkoxymethyl-substituted isoxazolines has also been probed in order to further expand the use of these heterocycles as aldol equivalents in natural products total synthesis.A synthesis of (+/-)-blastmycinone (34) is reported which combines the two foregoing aspects of stereocontrol.The levels of regio- and stereoselectivity found in the cycloaddition reactions of the cis- and trans-disubstituted alkenes 35 and 39 prepared from isopropylidene-D-glyceraldehyde are also discussed.A single example of the reaction of a chiral alkene with a chiral nitrile is presented.
Total Synthesis and Stereochemistry of (+)-Phyllanthocindiol
McGuirk, Paul R.,Collum, David B.
, p. 843 - 852 (2007/10/02)
The total synthesis of (+)-phyllanthocindiol starting with (S)-(+)-3-hydroxy-2-methylpropanoic acid and (S)-(-)-perilla aldehyde is reported.The totally enantioselective sequence elucidated the relative and absolute stereochemistry of (+)-phyllanthocindio
