78479-16-0Relevant academic research and scientific papers
Synthetic studies on bafilomycin A1: Stereoselective synthesis of the C12-C17 fragment and its coupling with the C 1-C11 subunit
Quéron, Emmanuelle,Lett, Robert
, p. 4533 - 4537 (2007/10/03)
Stereoselective addition of (E)-1-lithio-2-tributylstannylethylene on a chiral cyclic di-t-butylsilyleneketal C14-C17 aldehyde afforded the required Felkin-Anh adduct for the synthesis of the C 12-C17 fragment of bafilomycin A1, the configuration of which was assigned unambiguously. After appropriate coupling with the enantiopure C1-C11 fragment, the C 12-C17 subunit obtained here can be used for the study of the 16-membered macrolide formation either by an acyl activation or an intramolecular Stille reaction. Intermolecular esterification of the 15-OH with an acyl activation of the carboxylic acid of the C1-C11 fragment, in modified Yamaguchi's conditions, affords here an intermediate for examining an intramolecular Stille coupling.
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
A NEW SYNTHESIS OF (-)-Α-MULTISTRIATIN, THE PHEROMONE OF THE SMALLER EUROPEAN ELM BARK BEETLE
Mori, Kenji,Seu, Young-Bae
, p. 1035 - 1038 (2007/10/02)
(-)-Α-Multistriatinoctane> was synthesized from (Z)-2-butene-1,4-diol monobenzyl ether by employing the sharpless asymmetric epoxidation and the regioselective epoxide cleavage with Me3Al as the k
REGIOSELECTIVITY OF THE REACTIONS OF TRIALKYLALUMINUM REAGENTS WITH 2,3-EPOXYALCOHOLS: APPLICATION TO THE SYNTHESIS OF α-CHIRAL ALDEHYDES
Roush, William R.,Adam, Michael A.,Peseckis, Steven M.
, p. 1377 - 1380 (2007/10/02)
Treatment of optically active 2,3-epoxyalcohols with trialkylaluminum reagents followed by periodate cleavage constitutes a convenient synthesis of α-chiral aldehyde derivatives, especially when the branching alkyl group is methyl.
SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN
Mori, Kenji,Nomi, Hiroko,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
, p. 3705 - 3712 (2007/10/02)
The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by
Studies toward polyether antibiotics: stereospecific synthesis of polysubstituted tetrhydropyrans
Ho, Pak-Tsun
, p. 90 - 94 (2007/10/02)
A stereospecific and general method for the preparartion of trans-tetrahydropyrans 1 and cis-tetrahydropyrans 2 from acyclic precursors are described.Compound 12, a possible intermediate for the synthesis of antibiotic X-14547A, has been synthesized.
DETERMINATION OF THE ABSOLUTE CONFIGURATION AT C-6 AND C-7 SERRICORNIN (4,6-DIMETHYL-7-HYDROXY-3-NONANONE), THE SEX PHEROMONE OF THE CIGARETTE BEETLE
Mori, Kenji,Nomi, Hiroko /nee Iwasawa/,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
, p. 1127 - 1130 (2007/10/02)
The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 7S) by synthesizing its (6R, 7S)-erythro and (6R, 7R)-threo isomers.
