105608-29-5

Basic information

• Product Name: (4S,6R)-4-hydroxy-14-methyl-1,2,5,6-tetrahydro-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-3(4H)-one
• CAS NO: 105608-29-5
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.3472
• Mol File: 105608-29-5.mol

Chemical Properties

• Boiling Point: 531.5°C at 760 mmHg
• Flash Point: 275.3°C
• Density: 1.55g/cm³
• Vapor Pressure: 3.97E-12mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: (4S,6R)-4-hydroxy-14-methyl-1,2,5,6-tetrahydro-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,6R)-4-hydroxy-14-methyl-1,2,5,6-tetrahydro-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-3(4H)-one(105608-29-5)
• EPA Substance Registry System: (4S,6R)-4-hydroxy-14-methyl-1,2,5,6-tetrahydro-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-3(4H)-one(105608-29-5)

Safety Data

• Hazardous Substances Data: 105608-29-5(Hazardous Substances Data)

Upstream product

• 105608-27-3 (-)-prostephanaberrine 
• 1025023-05-5 (7β,8β,10β)-8,10-epoxy-7,8-dimethoxy-2,3-[methylenebis(oxy)]-17-methyl-6-oxohasubanan 

Relevant articles and documents

Development of enantioselective synthetic routes to the hasubanan and acutumine alkaloids

We describe a general strategy to prepare the hasubanan and acutumine alkaloids, a large family of botanical natural products that display antitumor, antiviral, and memory-enhancing effects. The absolute stereochemistry of the targets is established by an enantioselective Diels-Alder reaction between 5-(trimethylsilyl)cyclopentadiene (36) and 5-(2-azidoethyl)-2,3- dimethoxybenzoquinone (24). The Diels-Alder adduct 38 is transformed to the tetracyclic imine 39 by a Staudinger reduction-aza-Wittig sequence. The latter serves as a universal precursor to the targets. Key carbon-carbon bond constructions include highly diastereoselective acetylide additions to the N-methyliminium ion derived from 39 and Friedel-Crafts and Hosomi-Sakurai cyclizations to construct the carbocyclic skeleton of the targets. Initially, this strategy was applied to the syntheses of (-)-acutumine (4), (-)-dechloroacutumine (5), and four hasubanan alkaloids (1, 2, 3, and 8). Herein, the synthetic route is adapted to the syntheses of six additional hasubanan alkaloids (12, 13, 14, 15, 18, and 19). The strategic advantage of 5-(trimethylsilyl)cyclopentadiene Diels-Alder adducts is demonstrated by site-selective functionalization of distal carbon-carbon π-bonds in the presence of an otherwise reactive norbornene substructure. Evaluation of the antiproliferative properties of the synthetic metabolites revealed that four hasubanan alkaloids are submicromolar inhibitors of the N87 cell line.