132364-23-9Relevant articles and documents
Asymmetric synthesis of C11-C23 fragment of Pladienolide B
Khatun, Sanjida,Mainkar, Prathama Satyendra,Chandrasekhar, Srivari
, p. 717 - 722 (2014/07/07)
Synthesis of C11-C23 fragment of an antitumor natural product, Pladienolide B, in gram-scale, is described. The key steps involved in this synthesis are Julia-Kocienski olefination, opening of epoxide with TBSOTf to form the corresponding - OTBS protected
Synthesis of optically active β- Or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents
Guduguntla, Sureshbabu,Fananas-Mastral, Martin,Feringa, Ben L.
, p. 8274 - 8280 (2013/09/24)
An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols.
Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A
Donohoe, Timothy J.,O'Riordan, Timothy J. C.,Peifer, Manuel,Jones, Christopher R.,Miles, Timothy J.
, p. 5460 - 5463,4 (2012/12/12)
The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO4 catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.
Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A
Donohoe, Timothy J.,O'Riordan, Timothy J. C.,Peifer, Manuel,Jones, Christopher R.,Miles, Timothy J.
, p. 5460 - 5463 (2013/01/15)
The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO4 catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.
Process for total synthesis of pladienolide B and pladienolide D
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Page/Page column 34, (2010/11/29)
[Problems to be Solved] To provide an effective process for total synthesis of pladienolide B and pladienolide D having excellent anti-tumor activity and to provide useful intermediates in the above-described process. [Measure for Solving the Problem] A process for producing a compound represented by Formula (11): wherein P1, P7, P8, P9 and R1 are the same as defined below, characterized by including reacting a compound represented by Formula (12): wherein P7 means a hydrogen atom or a protecting group for hydroxy group; R1 means a hydrogen atom or a hydroxy group, with a compound represented by Formula (13): wherein P1 means a hydrogen atom or a protecting group for hydroxy group; P8 means a hydrogen atom, an acetyl group or a protecting group for hydroxy group; P9 means a hydrogen atom or a protecting group for hydroxy group; or P8 and P9 may form together a group represented by a formula: wherein R5 means a phenyl group which may have a substituent, in the presence of a catalyst.
Synthetic studies toward amphidinolide H1: Segment C14-C26
Deng, Lisheng,Ma, Zhixiong,Zhang, Yazhu,Zhao, Gang
, p. 87 - 90 (2008/03/13)
Stereoselective synthesis of the C14-C26 moiety of amphidinolide H1 is described. The key features of the approach include the convergent fragment assembly with a highly diastereoselective aldol reaction to establish the C18 stereochemistry and using comm
Total synthesis of the potent antitumor macrolides pladienolide B and D
Kanada, Regina M.,Itoh, Daisuke,Nagai, Mitsuo,Niijima, Jun,Asai, Naoki,Mizui, Yoshiharu,Abe, Shinya,Kotake, Yoshihiko
, p. 4350 - 4355 (2008/03/12)
Getting cross: The total syntheses of two pladienolides (see picture), which have prominent antitumor activity based on a unique mechanism of action, have been accomplished, and their absolute configurations were verified. The 12-membered aliphatic macrolide structure was formed by ring-closing metathesis, and the side-chain moiety was coupled to the macrolide by Julia-Kocienski olefination or cross-metathesis. (Chemical Equation Presented).
Synthesis of optically active bifunctional building blocks through enantioselective copper-catalyzed allylic alkylation using Grignard reagents
Van Zijl, Anthoni W.,Lopez, Fernando,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 2558 - 2563 (2007/10/03)
Enantioselective copper-catalyzed allylic alkylations were performed on allylic bromides with a protected hydroxyl or amine functional group using several Grignard reagents and Taniaphos L1 as a ligand. The terminal olefin moiety in the products was transformed into various functional groups without racemization, providing facile access to a variety of versatile bifunctional chiral building blocks.
Total synthesis of ( - )-cylindrocyclophanes A and F exploiting the reversible nature of the olefin cross metathesis reaction
Smith III,Adams,Kozmin,Paone
, p. 5925 - 5937 (2007/10/03)
Efficient total syntheses of the C2-symmetric ( - )-cylindrocyclophanes A and F (1a and 1f) have been achieved. The initial strategy featured the use of a common advanced intermediate to assemble in stepwise fashion the required macrocycle of 1f, exploiting in turn a Myers reductive coupling followed by ring-closing metathesis. In a second-generation strategy, a remarkable cross olefin metathesis dimerization cascade was discovered and exploited to assemble the requisite [7,7]-paracyclophane macrocycles of both 1a and 1f from dienyl monomers. The successful syntheses also featured the effective use of the Danheiser annulation to construct substrates for both the Myers reductive coupling and the metathesis dimerizations strategies. Finally, the Kowalski two-step chain homologation of esters to siloxyalkynes proved superior over the original one-step protocol.
