80184-02-7Relevant academic research and scientific papers
Spirastrellolide E: Synthesis of an advanced C(1)-C(24) southern hemisphere
Sokolsky, Alexander,Wang, Xiaozhao,Smith, Amos B.
, p. 3160 - 3164 (2015)
The synthesis of a C(1)-C(24) advanced southern hemisphere fragment towards the total synthesis of spirastrellolide E has been achieved. Highlights of the route include a highly convergent Type I Anion Relay Chemistry (ARC) tactic for fragment assembly, in conjunction with a directed, regioselective gold-catalyzed alkyne functionalization to generate the central unsaturated [6,6]-spiroketal.
Total synthesis of the polyene macrolide antibiotic roxaticin. I. Synthesis of the polyol fragment of roxaticin using a four-carbon chain extension strategy
Mori, Yuji,Asai, Motoya,Okumura, Akiko,Furukawa, Hiroshi
, p. 5299 - 5314 (2007/10/02)
The C11-C26 polyol fragment of roxaticin containing eight chiral centers has been prepared in a reiterative manner using coupling reactions of chiral dithianes and epoxides followed by stereoselective reduction.
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
SYNTHESYS OF THE C11-C28 SUBUNIT OF THE AVERMECTINS
Hirama, Masahiro,Nakamine, Takeshi,Ito, Sho
, p. 1197 - 1198 (2007/10/02)
Construction of the trisubstituted double bond of the C11-C28 subunit of avermectin A1a and B1a has been achieved in a five-step sequence.
Enantioselective total synthesis of ingramycin
Tanner, David,Somfai, Peter
, p. 4395 - 4406 (2007/10/02)
An enantioselective total synthesis of the 14-membered macrolide antibiotic ingramycin, 1, is described. In a convergent approach three chiral fragments A,B and C are assembled, the allylic bromide A deriving its chirality from L-serine while the asymmetr
Total Synthesis of Ionophore Antibiotic X-14547A
Nicolaou, K. C.,Papahatjis, D. P.,Claremon, D. A.,Magolda, R. L.,Dolle, R. E.
, p. 1440 - 1456 (2007/10/02)
A highly stereocontrolled and convergent total synthesis of optically active ionophore antibiotic X-14547A (1) was designed and carried out.Degradative reactions led to the key intermediates 3 and 6, which served as convenient comparison stages.The tetrah
Enantiomerically Pure Building Blocks for Syntheses from Branched Malates
Aebi, Johannes D.,Sutter, Marius A.,Wasmuth, Daniel,Seebach, Dieter
, p. 2114 - 2126 (2007/10/02)
Isocitric acid lactone (13) and the chiral building blocks (2S,3R)-4-bromo-1,2-epoxy-3-methyl-butane (21), cis- and trans 2,3-epoxy-2-methylsuccinates (23, 24), and the singly protected (2R)-2-methyl-, -2-allyl- and -2-benzyl-1,3-propanediols (32a, b, c)
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.
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.
