66513-28-8

Usage

InChI:InChI=1/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23-,24+,25+,27?,28+,30+/m0/s1

Upstream product

• 76567-01-6 Indanomycin methyl ester 
• 76567-01-6 (-)-methyl α(R),5(S)-dimethyl-6(R)-<1-ethyl-4-<4(S)-(2-pyrrolylcarbonyl)-1(S)-ethyl-3a(R),4,5(S),7a(S)-tetrahydroindan-5-yl>-1(E),3(E)-butadienyl>tetrahydropyran-2(R)-acetate 
• 105164-33-8 ((1S,3aR,4S,5S,7aS)-1-Ethyl-5-{(1E,3E)-4-[(2R,3S,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-hexa-1,3-dienyl}-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl)-(1H-pyrrol-2-yl)-methanone 
• 153868-68-9 (αR,2R,5S,6R)-α,5-Dimethyl-6-<(1E)-1-ethyl-2-iodovinyl>tetrahydropyran-2-acetic acid 
• 88204-55-1 (R)-2-((2R,5S)-5-Methyl-6-methylene-tetrahydro-pyran-2-yl)-propionic acid methyl ester 
• 91053-96-2 methyl α(R),5(S)-dimethyl-6(S)-(iodomethyl)tetrahydropyran-2(R)-acetate 
• 88204-57-3 methyl α(R),5(S)-dimethyl-6(R)-formyltetrahydropyran-2(R)-acetate 
• 88204-65-3 C₅₁H₆₉NO₉SSi 
• 88204-54-0 methyl α(R),5(S)-dimethyl-6(S)-(hydroxymethyl)tetrahydropyran-2(R)-acetate 
• 88204-56-2 methyl α(R),5(S)-dimethyl-6(R)-(hydroxymethyl)tetrahydropyran-2(R)-acetate 
• 76566-89-7 (+/-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone 
• 76566-84-2 methyl (αR,2R,5S,6R)-tetrahydro-α,5-dimethyl-6-(1-oxopropyl)-2H-pyran-2-acetate 
• 76566-87-5 methyl (αR,2R,5S,6R)-6-<(E)-1-ethyl-2-formylvinyl>tetrahydro-α,5-dimethyl-2H-pyran-2-acetate 
• 88204-61-9 (1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide 

Downstream Products

• 80109-54-2 (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1R,3aS,4R,5S,7aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 
• 80109-54-2 (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of Ionophore Antibiotic X-14547A (Indanomycin)

A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described.The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the "left wing" fragment 2.Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 -> 25 -> 26) via net SN2' coupling of silanes with Grignard reagents catalyzed by CuCN.Salient features in the construction of the "right wing" subunit 3 include a modification of the Noyori three-component coupling procedure (32 -> 33) and the application of a retro hetero Diels-Alder/intramolecular Diels-Alder ("mock Claisen") process (5 -> 39).Palladium-mediated cross coupling of "left wing" and "right wing" synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

An Efficient Enantioselective Total Synthesis of (-)-X-14547A (Indanomycin)

A highly efficient and stereocontrolled enantioselective total synthesis of the antibiotic ionophore X-14547A (indanomycin) (1) is described.A particulary concise approach to the key pyranaldehyde intermediate 3 features the use of reductive lithiation to append the axial C(7) pyran side chain.A Wittig reaction was employed to couple the two major subunits 3 and 4 followed by intramolecular cycloaddition to complete the framework.

Ionophore Antibiotic X-14547A. Degradation Studies and Stereoselective Construction of the "Right Wing" (C11-C25 Fragment) by an Intramolecular Diels-Alder Reaction

Studies directed toward the total synthesis of the ionophore antibiotic X-14547A are reported.Degradation methods led to a number of "left-wing" fragments, whereas synthetic operations led to a "right- wing" fragment, in a highly efficient and stereoselec