66550-09-2

Basic information

• Product Name: Muzigadial
• Synonyms: (1S)-1,4,4aα,5,6,7,8,8a-Octahydro-1α-hydroxy-6β,8aβ-dimethyl-5-methylene-1,2-naphthalenedicarbaldehyde
• CAS NO: 66550-09-2
• Molecular Formula: C15H20O3
• Molecular Weight: 248.32
• Product Categories: Miscellaneous Natural Products
• Mol File: 66550-09-2.mol

Chemical Properties

• Boiling Point: 389.4°C at 760 mmHg
• Flash Point: 203.5°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 1.13E-07mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: Muzigadial(CAS DataBase Reference)
• NIST Chemistry Reference: Muzigadial(66550-09-2)
• EPA Substance Registry System: Muzigadial(66550-09-2)

Safety Data

• Hazardous Substances Data: 66550-09-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O3/c1-10-6-7-14(3)13(11(10)2)5-4-12(8-16)15(14,18)9-17/h4,8-10,13,18H,2,5-7H2,1,3H3/t10-,13-,14-,15+/m0/s1

Upstream product

• 100432-40-4 1-hydroxy-2-(dimethoxymethyl)-6β,8aβ-dimethyl-5-methylene-trans-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxaldehyde 

Relevant articles and documents

A Stereoselective Total Synthesis of (+/-)-Muzigadial

A stereoselective 14-step, total synthesis of (+/-)-muzigadial (1a, 11percent overall yield), starting from the commercially available Wieland-Miescher ketone (5), via intermediate ketone 13, is described.The two additional chiral centers in 13 were incorporated by equilibrium of the mixture of stereoisomeric ketones 10 to the most favorable isomer, 10a.The key step for introducing the necessary functionality at C-1 involved the regio- and stereoselective cis hydroxylation of enol ether 37b with osmium tetraoxide in the presence of tert-butyl hydroperoxide.