72229-13-1Relevant 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 (+)-isolaurepinnacin
Suzuki, Toshio,Matsumura, Ryuji,Oku, Ken-ichi,Taguchi, Keiichi,Hagiwara, Hisahiro,Hoshi, Takashi,Ando, Masayoshi
, p. 65 - 67 (2007/10/03)
The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the α,ω-positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)2O/Zn(OTf)2 system.
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
STUDIES ON THE SYNTHESIS OF THE APLYSIATOXINS: SYNTHESIS OF A SELECTIVELY-PROTECTED FORM OF THE C27-C30 (DIHYDROXYBUTANOATE) MOIETY OF OSCILLATOXIN A
Walkup, Robert D.,Cunningham, Raymond T.
, p. 4019 - 4022 (2007/10/02)
A protected form of (R)-3,4-dihydroxybutanoic acid bearing a benzyl protecting group at the C4 hydroxyl and a dimethylthexylsilyl protecting group at the C3 hydroxyl was synthesized via a selective Ag(I)-mediated monobenzylation of (R)-methyl 3,4-dihydroxybutanoate.An alternative synthetic route from a chiral allylic ether was successful but problematic.The acid could be clenly coupled to a model for the C3-C11 moiety of the aplysiatoxins.
