83803-81-0Relevant articles and documents
Toward Leiodermatolide: Synthesis of the Core Structure
Reiss, Anita,Maier, Martin E.
supporting information, p. 3146 - 3149 (2016/07/13)
The macrocyclic core (35) of the marine natural product leiodermatolide (1) was synthesized from two key fragments, vinyl iodide 23 (C1-C11 part) and vinyl stannane 31 (C12-C18 part). A Stille coupling led to conjugated Z,Z-diene 32. The derived seco acid 34 was cyclized using a Yamaguchi macrolactonization. Key steps in the assembly of vinyl iodide 23 were a Paterson aldol reaction, and a Kumada coupling on a triflate derivative to create the C4-C5 trisubstituted double bond. The two stereocenters in fragment 31 were established by a Marshall-Tamaru reaction. The longest linear sequence comprises 20 steps.
Process for total synthesis of pladienolide B and pladienolide D
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Page/Page column 27-28, (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.
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).
Simple, Catalytic Enantioselective Syntheses of Estrone and Desogestrel
Hu, Qi-Ying,Rege, Pankaj D.,Corey
, p. 5984 - 5986 (2007/10/03)
Highly enantioselective and very short syntheses of the bioactive forms of estrone (3) and desogestrel (4) are described using a chiral oxazaborolidinium catalyst (2) in the key initial step. Enantiomerically pure estrone was synthesized in eight steps from the readily available starting materials diene 5 and α,β-enal 6 via intermediates 8 and 9. Desogestrel was synthesized using a similar strategy from diene 5 and α,β-enal 11 via intermediates 12-17. The efficient syntheses of the chiral catalyst 2 and its enantiomer are also presented. Copyright
Triene compounds having a chromene structure
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, (2008/06/13)
Compounds of general formula (I): STR1 in which: R1, R2, R3 and R4, which may be identical or different, denote a hydrogen atom, a halogen atom or a lower alkyl, lower alkenyl, lower alkyloxy or lower alkenyloxy group, optionally substituted with one or more halogen atoms, R5 denotes a carboxyl, (lower alkyloxy)carbonyl, (lower alkenyloxy)carbonyl or (lower alkynyloxy)-carbonyl, their isomers, stereoisomers and diastereoisomers, and also their addition salts with a pharmaceutically acceptable base. Medicinal products.
Synthesis of New Aromatic Retinoid Analogues by Low-Valent Titanium Induced Reductive Elimination
Solladie, Guy,Girardin, Andre,Lang, Gerard
, p. 2620 - 2628 (2007/10/02)
The low-valent titanium reductive elimination reaction, already applied to the stereospecific synthesis of vitamin A and 13-cis-retinol, was used to prepare several retinoic acid analogues in the all-trans configuration or in the 13-cis configuration.This highly stereospecific trans-diene formation allowed an improved synthesis of the title compounds without any purification of the intermediates before the final stage.
HIGHLY STEREOSELECTIVE SYNTHESIS OF VITAMIN A AND ALL-TRANS RETINOIC ACID BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
Solladie, Guy,Girardin, Andre
, p. 213 - 216 (2007/10/02)
Application of the low-valent Titanium induced reductive elimination gave a new and highly stereoselective approach to vitamin A and all-trans retinoic acid.
A NEW SYNTHESIS OF Δ2-BUTENOLIDES VIA STEREOSELECTIVE FORMATION OF α,β-ETHYLENIC ESTERS
Larcheveque, M.,Legueut, Ch.,Debal, A.,Lallemand, J. Y.
, p. 1595 - 1598 (2007/10/02)
A new synthesis of Δ2-butenolides is described which involves stereoselective condensation of an α-silyl ester anion with an α-ketoacetal.