184877-64-3

Basic information

• Product Name: madindoline A
• Synonyms: madindoline A
• CAS NO: 184877-64-3
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.45408
• Mol File: 184877-64-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: madindoline A(CAS DataBase Reference)
• NIST Chemistry Reference: madindoline A(184877-64-3)
• EPA Substance Registry System: madindoline A(184877-64-3)

Safety Data

• Hazardous Substances Data: 184877-64-3(Hazardous Substances Data)

Upstream product

• 888020-75-5 (3aR,8aS)-3a-(tert-butyldimethylsilyloxy)-8-(2-methoxycarbonylpropyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 
• 405297-75-8 (E)-2-Trimethylsilanylmethyl-hept-2-enoyl chloride 
• 912833-56-8 (Z)-2-Methyl-3-oxo-4-trimethylsilanylmethyl-non-4-enoic acid methyl ester 
• 17598-10-6 1-morpholin-4-yl-hexan-1-one 
• 929286-93-1 C₂₂H₄₂O₄Si 
• 929286-92-0 C₁₇H₃₄O₂Si 
• 929286-91-9 C₂₀H₃₉NO₃Si 
• 929287-04-7 C₂₃H₃₁NO₂SSi 
• 929287-03-6 C₁₆H₂₅NO₂Si 
• 929286-96-4 C₂₆H₅₂O₂Si₂ 
• 929286-94-2 C₂₀H₃₆O₂Si 
• 391612-42-3 (3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate 
• 912833-58-0 (Z)-2-((3aR,8aS)-3a-Hydroxy-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl)-2-methyl-3-oxo-4-trimethylsilanylmethyl-non-4-enoic acid methyl ester 
• 261785-61-9 (2'R)-1-[4-(n-butyl)-2,5-dimethyl-1,3-dioxo-2-(4-cyclopentenyl)methyl]-3-(2-hydroxyethyl)indoline 

Relevant articles and documents

Total synthesis of madindoline A

The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)2-NaBH(OAc)3. After the redu

Determination of the absolute stereochemistry and asymmetric total synthesis of madindolines A and B: A practical improvement to a second-generation approach from the first-generation

In this report, we describe an efficient, highly convergent, stereocontrolled first total synthesis and a second-generation synthesis of madindolines A 1 and B 2, potent selective inhibitors of interleukin 6. The key steps include (1) asymmetric oxidative ring-closure reaction of tryptophol 3 to construct a chiral 3a-hydroxyfuroindoline 4 using the modified Sharpless asymmetric epoxidation condition, (2) highly diastereoselective acylation to build up the quaternary carbon center, and (3) intramolecular acylation of ester 32 with allylsilanes to produce the full substituted cyclopentenedione units. Our first synthetic route defines for the first time both their relative and absolute configurations. Moreover, a more efficient second-generation synthesis was designed, which is suitable for gram-scale preparation of these compounds.

Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B

A three-component Mannich reaction of 3a-hydroxyfuroindoline (3), β-ketoester and formaldehyde was employed as an efficient and concise method to synthesize naturally-occurring (+)-Madindolines A (1) and B (2). The scope and limitations of the Mannich rea

Synthesis of (+)-madindoline A and (+)-madindoline B

The allene ether version of the Nazarov cyclization was used to construct the cyclopentane dione portion of madindolines A and B. The racemic cyclopentane dione from the Nazarov cyclization was converted to an enol ether that was combined with the chiral,

Design, synthesis, and biological activities of madindoline analogues

A research program is under way to develop a series of madindoline-based inhibitors targeting interleukin 6. Such inhibitors will have potential use in fighting a variety of diseases for which no effective therapeutic drugs currently exist. Madindoline is