158761-02-5

Basic information

• Product Name: mniopetal E
• Synonyms: mniopetal E
• CAS NO: 158761-02-5
• Molecular Formula: C15H20 O6
• Molecular Weight: 296.32
• Mol File: 158761-02-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 548.6°Cat760mmHg
• Flash Point: 207.2°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 2.54E-14mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: mniopetal E(CAS DataBase Reference)
• NIST Chemistry Reference: mniopetal E(158761-02-5)
• EPA Substance Registry System: mniopetal E(158761-02-5)

Safety Data

• Hazardous Substances Data: 158761-02-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O6/c1-14(2)5-8(17)11(18)15-9(14)4-3-7(6-16)10(15)12(19)21-13(15)20/h3,6,8-12,17-19H,4-5H2,1-2H3/t8-,9-,10+,11-,12-,15+/m0/s1

Upstream product

• 252000-14-9 Bromo-acetic acid (7E,9E)-(3S,4S)-10-[1,3]dithiolan-2-yl-3,4-bis-methoxymethoxy-6,6-dimethyl-2-oxo-deca-7,9-dienyl ester 
• 252000-16-1 (1S,2R,3S,6S,9S,10S)-2,3-bis(methoxymethoxy)-5,5-dimethyl-9-(1,3-dithiolan-2-yl)-12-oxatricyclo[8.3.0.0^1,6]tridec-7-en-11-one 
• 252000-15-0 3-[(1S,2S,5E,7E)-1,2-bis(methoxymethoxy)-4,4-dimethyl-8-(1,3-dithiolan-2-yl)-5,7-octadienyl]-2-buten-4-olide 
• 315674-55-6 (R)-4-((5E,7E)-(1S,2S)-8-[1,3]Dithiolan-2-yl-1,2-bis-methoxymethoxy-4,4-dimethyl-octa-5,7-dienyl)-2,2-dimethyl-[1,3]dioxolane 
• 252000-13-8 (2R,3S,4S,7E,9E)-3,4-bis(methoxymethoxy)-6,6-dimethyl-10-(1,3-dithiolan-2-yl)-7,9-decadiene-1,2-diol 
• 252000-12-7 (2E,4E)-(8S,9S)-9-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8,9-bis-methoxymethoxy-6,6-dimethyl-nona-2,4-dienal 
• 199471-63-1 ethyl (2E,4E,8S,9S,10R)-8,9-bis(methoxymethoxy)-6,6-dimethyl-10,11-(isopropylidenedioxy)-2,4-undecadienoate 
• 199471-64-2 (2E,4E,8S,9S,10R)-8,9-bis(methoxymethoxy)-6,6-dimethyl-10,11-(isopropylidenedioxy)-2,4-undecadien-1-ol 
• 252000-22-9 (1R,2R,3S,6S,9S,10S,12R,15S)-2,3-bis(methoxymethoxy)-5,5-dimethyl-10-methoxy-11,13-dioxatetracyclo[10.2.1.0^1,6.0^9,15]pentadec-7-en-14-one 
• 252000-21-8 C₂₀H₃₂O₈ 
• 252000-18-3 (1S,2R,3S,6S,9S,10S)-2,3-bis(methoxymethoxy)-9-(dimethoxymethyl)-5,5-dimethyl-12-oxatricyclo[8.3.0.0^1,6]tridec-7-en-11-one 
• 199471-60-8 (E)-(6S,7S)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6,7-bis-methoxymethoxy-4,4-dimethyl-hept-2-enoic acid ethyl ester 
• 199471-62-0 (E)-(6S,7S)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6,7-bis-methoxymethoxy-4,4-dimethyl-hept-2-enal 
• 199471-61-9 (2E,6S,7S,8R)-6,7-bis(methoxymethoxy)-4,4-dimethyl-8,9-(isopropylidenedioxy)-2-nonen-1-ol 

Relevant articles and documents

Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.

Synthetic studies towards mniopetals (II). A short synthesis of Mniopetal E

A short total synthesis of Mniopetal E in thirteen steps is reported. Key steps are a new and highly diastereoselective lithium phenylselenide induced Baylis-Hillman reaction with Feringa's butenolide, an endo-selective intramolecular Diels-Alder reaction (IMDA) and a new variant of the Parikh-Doering oxidation.