68042-46-6

Basic information

• Product Name: (4bS,8aS)-4b,5,6,7,8,8a,9,10-Octahydro-1,4-dihydroxy-4b,8,8-trimethyl-2-phenanthrenecarbaldehyde
• Synonyms: (4bS,8aS)-4b,5,6,7,8,8a,9,10-Octahydro-1,4-dihydroxy-4b,8,8-trimethyl-2-phenanthrenecarbaldehyde;Premnolal
• CAS NO: 68042-46-6
• Molecular Formula: C18H24 O3
• Molecular Weight: 288.38
• Mol File: 68042-46-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4bS,8aS)-4b,5,6,7,8,8a,9,10-Octahydro-1,4-dihydroxy-4b,8,8-trimethyl-2-phenanthrenecarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (4bS,8aS)-4b,5,6,7,8,8a,9,10-Octahydro-1,4-dihydroxy-4b,8,8-trimethyl-2-phenanthrenecarbaldehyde(68042-46-6)
• EPA Substance Registry System: (4bS,8aS)-4b,5,6,7,8,8a,9,10-Octahydro-1,4-dihydroxy-4b,8,8-trimethyl-2-phenanthrenecarbaldehyde(68042-46-6)

Safety Data

• Hazardous Substances Data: 68042-46-6(Hazardous Substances Data)

Upstream product

• 15340-76-8 1,1,4aβ-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-10aα-phenanthren-6-ol 
• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 1224-26-6 12-methoxypodocarpa-8,11,13-trien-18-ol 
• 85852-96-6 12-hydroxypodocarpa-8,11,13-triene-13-carbaldehyde 
• 85852-97-7 12-methoxypodocarpa-8,11,13-triene-13-carbaldehyde 
• 85853-00-5 13-(acetoxymethyl)podocarpa-8,11,13-trien-12-ol 
• 85853-03-8 13-hydroxymethyl-12-methoxypodocarpa-8,11,13-trien-11-ol 
• 85853-04-9 13-hydroxymethyl-11,12-dimethoxypodocarpa-8,11,13-triene 
• 85852-99-9 ((4bS,8aS)-3-Methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl)-oxo-acetic acid 
• 85852-98-8 13-ethoxyoxalyl-12-methoxypodocarpa-8,11,13-triene 
• 57794-12-4 methyl 12-hydroxy-8,11,13-podocarpatrien-18-oate methyl ether 
• 85853-01-6 13-acetoxymethyl-11-nitropodocarpa-8,11,13-trien-12-ol 
• 85853-05-0 11,12-dimethoxypodocarpa-8,11,13-triene-13-carbaldehyde 
• 85853-02-7 13-acetoxymethyl-12-methoxy-11-nitropodocarpa-8,11,13-triene 

Relevant articles and documents

The Synthesis of (+)-Premnolal

The revised structure of premnolal was confirmed by the following synthesis.Treatment of 12-methoxypodocarpa-8,11,13-triene (7), derived from methyl 12-methoxypodocarpa-8,11,13-trien-18-oate, with ethoxyoxalyl chloride and anhydrous aluminium chloride afforded 13-(ethoxyoxalyl) derivative, which was converted into 12-hydroxypodocarpa-8,11,13-triene-13-carbaldehyde (9) by alkaline hydrolysis, decarboxylation, and demethylation.The compound 9 was also prepared from 7 by demethylation and formylation.Reduction of 9 with lithium aluminium hydride, followed by partial acetylation, afforded 13-acetoxymethyl derivative which was converted into 13-acetoxymethyl-12-methoxy-11-nitropodocarpa-8,11,13-triene by nitration and methylation.This was then converted into 11,12-dimethoxypodocarpa-8,11,13-triene-13-carbaldehyde (18) by a series of reactions: catalytic hydrogenation, diazotization, reduction with lithium aluminium hydride, methylation, and oxidation.Demethylation of 18 gave 11,12-dihydroxypodocarpa-8,11,13-triene-13-carbaldehyde, which was identical with natural premnolal.