72229-15-3Relevant academic research and scientific papers
Stereoselective synthesis of tetrahydropyrans through tandem and organocatalytic oxa-Michael reactions: Synthesis of the tetrahydropyran cores of ent-(+)-sorangicin A
Lee, Kiyoun,Kim, Hyoungsu,Hong, Jiyong
, p. 1025 - 1032 (2012/03/27)
Tandem and organocatalytic oxa-Michael reactions of α,β- unsaturated aldehydes were explored for the stereoselective synthesis of structurally complex tetrahydropyrans. Thestereoselective synthesis of 2,6-trans-tetrahydropyrans, which are thermodynamically unfavorable, was accomplished through a reagent-controlled, organocatalytic oxa-Michael reaction. A temperature-dependent configurational switch allowed the preparation of both 2,3-trans-2,6-trans-and 2,3-cis-2,6-cis-tetrahydropyrans from a common substrate. This switch was then used to synthesize the precursors of the C21-C29 and C30-C37 fragments of ent-(+)-sorangicin A. The tandem and organocatalytic oxa-Michael reactions of α,β-unsaturated aldehydes were explored and applied to the stereoselective synthesis of structurally complex tetrahydropyrans. Copyright
Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: Total synthesis of psymberin
Byeon, Seong Rim,Park, Heekwang,Kim, Hyoungsu,Hong, Jiyong
supporting information; experimental part, p. 5816 - 5819 (2012/01/06)
The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of α,β-un
Formal Synthesis of a Unsaturated Trihydroxy C-18 Fatty Acid
Sharma, Pradeep Kumar
, p. 1825 - 1826 (2007/10/02)
Stereoselective synthesis of (4R,5S)-2,2-dimethyl-5--1,3-dioxolane-4-carboxaldehyde, a key intermediate for the synthesis of (9S, 12S, 13S)-trihydroxy-(10E, 15Z)-octadecadienoic acid starting from cis-butene-1,4-diol, is described.
An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons
Trost, Barry M.,Nuebling, Christoph
, p. 1 - 12 (2007/10/02)
An asymmetric synthesis of 6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine and its α anomer from non-carbohydrate building blocks is achieved in 7 steps.The sequence builds the basic structures using bis(methylthio)methane and methylthiomethyl phenyl sulfone as
Isomer Selectivity in Stereocontrolled Payne Rearrangement-epoxide Cleavage of 2,3-Epoxy Alcohols in Aprotic Solvents: Application to an Enantioselective Total Synthesis of (+)-exo-Brevicomin
Page, Philip C. Bulman,Rayner, Christopher M.,Sutherland, Ian O.
, p. 1375 - 1382 (2007/10/02)
Organo-copper and -cuprate reagents may be used to trap the more reactive epoxy alkoxide isomer in a Lewis acid-catalysed Payne rearrangement process.This methodology has been used as the key step in a five-step enantioselective total synthesis of (+)-exo
GENERAL METHOD TO TRANSFORM CHIRAL 2,3-EPOXYALCOHOLS INTO ERYTHRO OR THREO 1,2-EPOXYALCOHOLS WITH TOTAL STEREOCHEMICAL CONTROL
Palazon, J. M.,Anorbe, B.,Martin, V. S.
, p. 4987 - 4990 (2007/10/02)
The isomerization of chiral 2,3-epoxyalcohols from E-allylic alcohols to chiral erythro or threo 1,2-epoxyalcohols has been accomplished with good yields, perfect stereochemical control and a very high grade of generality.
Chiral Electrophilic Synthetic Building Blocks with Four Different Functional Groups from Tartaric Acid, 2,3- and 3,4-Epoxy-butanediol Derivatives in All Four Stereoisomeric Forms
Hungerbuehler, Ernst,Seebach, Dieter
, p. 687 - 702 (2007/10/02)
Efficient and simple procedures have been developed for the preparation of the threo- and erythro-3,4-epoxy-1,2-butanediol derivatives 7 and 9 in both enantiomeric forms from tartaric acid.These epoxides should prove versatile as alkylating reagents in sy
