40709-29-3

Usage

InChI:InChI=1/C19H37NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h16-18,20-21H,3-15H2,1-2H3/t16-,17-,18+,19-/m1/s1

Upstream product

• 82042-24-8 (6R,7S,8S)-7-butyl-8-hydroxy-2-pentyl-1-azaspiro<5.5>undec-1-ene 
• 120851-30-1 8-Oxoperhydrohistrionicotoxin 
• 34272-51-0 (-)-histrionicotoxin 
• 34272-52-1 isodihydrohistrionicotoxin 
• 219986-35-3 (2R,3R,6S,7S,9R)-6-Butyl-11-oxo-9-pentyl-2,3-diphenyl-1,4-dioxa-8-aza-dispiro[4.1.5.3]pentadecane-8-carboxylic acid benzyl ester 
• 82042-15-7 (6S,7S,8S)-7-butyl-8-hydroxy-1-azaspiro<5.5>undecan-2-one 
• 693-25-4 n-pentylmagnesium bromide 
• 55228-76-7 (6SR,7SR,8SR)-7-n-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-one 
• 82042-20-4 (6S,7S,8S)-7-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-thione 
• 81992-01-0 (-)-(S)-<(6S,7S,8S)-7-butyl-2-oxo-1-azaspiro<5.5>undec-8-yl> N-(1-phenylethyl)carbamate 
• 118015-99-9 (R)-5-Pentyl-2-pyrrolidinone 
• 120790-99-0 C₁₇H₃₁NO₂ 
• 120791-07-3 (2R,6R,7S,8R)-7-((E)-But-2-enyl)-2-pentyl-1-aza-spiro[5.5]undecan-8-ol 
• 120791-06-2 C₁₇H₂₉NO₂ 

Relevant academic research and scientific papers

A gram-scale batch and flow total synthesis of perhydrohistrionicotoxin

The total synthesis of the spi- ropiperidine alkaloid (-)-perhydrohis- trionicotoxin (perhydro-HTX) 2 has been accomplished on a gram scale by employing both conventional batch chemistry as well as microreactor techniques. )-6-Pentyltetrahydro- pyran-2-one 8 underwent nucleophilic ring opening to afford the alcohol 10, which was elaborated to the nitrone 13. Protection of the nitrone as the 1,3- adduct of styrene and side-chain extension to the unsaturated nitrile afforded a precursor 17, which underwent dipolar cycloreversion and 1,3-dipolar cycloaddition to give the core spirocyclic precursor 18 that was converted into perhydro-HTX 2. The principal steps to the spirocycle 18 have successfully been transferred into flow mode by using different types of microreactors and in a telescoped fashion, allowing for a more rapid access to the histrioni- cotoxins and their analogues by continuous processing.

Total synthesis of (-)-histrionicotoxin 285A and (-)- perhydrohistrionicotoxin

(Chemical Equation Presented) Starting from commercially available (S)-glycidol, and via a common intermediate, the total synthesis of (-)-histrionicotoxin 285A and (-)-perhydrohistrionicotoxin has been achieved. Key to this synthesis was the efficient co

A two-directional synthesis of (+/-)-perhydrohistrionicotoxin.

An entirely two-directional synthesis of (+/-)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (+/-)-histrionicotoxin and (+/-)-histrionicotoxin 235A.

A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-epi-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones

(Matrix Presented) A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(±)-perhydrohistrionicotoxin with high diastereomeric contro

Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones: Asymmetric synthesis of (-)-perhydrohistrionicotoxin

The first chiral auxiliary-mediated asymmetric synthesis of (-)-perhydrohistrionicotoxin is described.

A Stereoselective Synthesis of (-)-Perhydrohistrionicotoxin

The first synthesis of (-)-perhydrohistrionicotoxin, 2, which proceeds without recourse to resolution of synthetic intermediates is reported.The absolute stereochemistry is derived from L-glutamic acid, and the key step, in which the critical relative ste

Highly Stereoselective Ring Contraction of Heterocyclic Enamines: Total Synthesis of Perhydrohistrionicotoxin and Its 2,6-Epimer

The total syntheses of perhydrohistrionicotoxin (PHTX) and its 2,6-epimer in which the pentyl group, introduced in the early stages, controls the relative configuration of C6 in a highly stereoselective manner are described.Seven-membered heterocyclic ena

THE STEREOCHEMISTRY OF SPIROPIPERIDINE CYCLIZATIONS (HISTRIONICOTOXIN, PART I)

The spirocyclization of straight-chain triketo-intermediates, similar to possible biogenetic precursors of histrionicotoxin, is shown to be stereoselective, generating the non-natural configuration at C-2.Aiming at an sp2-center in this positio