127681-58-7

Basic information

• Product Name: 9alpha,11-Dihydroxydrim-7-en-6-one
• Synonyms: 9alpha,11-Dihydroxydrim-7-en-6-one;9α,11-Dihydroxydrim-7-en-6-one
• CAS NO: 127681-58-7
• Molecular Formula: C15H24O3
• Molecular Weight: 252.34926
• Mol File: 127681-58-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9alpha,11-Dihydroxydrim-7-en-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9alpha,11-Dihydroxydrim-7-en-6-one(127681-58-7)
• EPA Substance Registry System: 9alpha,11-Dihydroxydrim-7-en-6-one(127681-58-7)

Safety Data

• Hazardous Substances Data: 127681-58-7(Hazardous Substances Data)

Upstream product

• 127681-57-6 7,9-drimadien-6-one 
• 110547-82-5 6-oxo-7-drimen-11-ol acetate 
• 74635-87-3 6-oxo-7-drimen-11-ol 
• 74636-06-9 (+)-uvidin A 
• 326795-30-6 (1S,3R,4S,4aR,8aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3,4a,8,8-tetramethyldecahydronaphthalene-1,3-diol 
• 326795-31-7 (3R,4S,4aR,8aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-hydroxy-3,4a,8,8-tetramethyloctahydronaphthalen-1(2H)-one 
• 127681-59-8 (4S,4aR,8aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 
• 326795-16-8 (1S,3R,4R,4aS,8aS)-3-(Acetyloxy)-4-formyl-3,4a,8,8-tetramethyldecahydronaphthalen-1-yl acetate 
• 326795-29-3 (1S,3R,4S,4aS,8aS)-4-(Hydroxymethyl)-3,4a,8,8-tetramethyldecahydronaphthalene-1,3-diol 
• 74635-87-3 (4S,4aR,8aS)-4-(Hydroxymethyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 
• 110547-82-5 ((1S,4aS,8aR)-2,5,5,8a-Tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate 
• 127681-57-6 (4aS,8aS)-3,4a,8,8-Tetramethyl-4-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 

Downstream Products

• 23599-45-3 (-)-cinnamodial 
• 110557-39-6 (-)-epi-Albrassitriol 
• 110557-39-6 (-)-Albrassitriol 
• 192566-65-7 (5S,6S)-5-hydroxy-4,5-di(hydroxymethyl)-6,10,10-trimethylbicyclo[4.4.0]dec-3-en-2-one 

Relevant articles and documents

SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE NATURAL COMPOUNDS. PART I: STEREOSPECIFIC TRANSFORMATION OF UVIDIN A INTO (-)-CINNAMODIAL

A partial synthesis of (-)-cinnamodial (1) has been achived, using (+)-uvidin A (3) as starting material.This also represents a formal synthesis of (-)-cinnamosmolide (2a) and pereniporin B (2b).

Formal synthesis of (-)-pereniporin B and (-)-cinnamosmolide

The paper describes a new pathway for an efficient synthesis of natural and bioactive drimanic compounds (-)-pereniporin B (1) and (-)-cinnamosmolide (2) from ketodiol 7, an intermediate obtained before from accessible labdane diterpenoid (+)-larixol (3). The key step involves allylic bromination of acetate 8 with N-bromosuccinimide. The in vitro antimicrobial and antifungal activities of all compounds are also reported. Their structures were confirmed by both spectroscopic data and chemical transformations.

Synthesis of (-)-albrassitriol and (-)-6-epi-albrassitriol from (+)-larixol

A novel synthesis of natural drimanic compounds, (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), has been carried out starting from an easily available labdane diterpenoid, (+)-larixol (1). In a two-step procedure, (+)-larixol (1) was converted into 14,15-bisnorlab-7-ene-6,13-dione (9), which was then submitted to a Norrish type II photochemical degradation yielding drim-7,9(11)-diene-6-one (10), whose treatment with OsO4 led selectively to the formation of drim-7-ene-9α,11-diol-6-one (12). The same compound was obtained by selective epoxidation of the C(9)-C(11) double bond in drim-7,9(11)-diene-6-one (10) with monoperphtalic acid. Treatment of the resulting mixture of α-and β-epoxides (13 and 14) with HClO 4 yielded drim-7-ene-9α,11-diol-6-one (12). Reduction of the C6-carbonyl group in drim-7-ene-9α,11-diol-6-one (12) with LiAlH 4 afforded (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), 12.4% and 13.6% overall yields, respectively.

Synthesis of drimanes from (+)-larixol

The selective transformation of the side chain of larixol 1 to a functionalized one-carbon moiety leads to 6,8-diacetoxydrimenal 13, which was converted to the drimanes (-)-albrassitriol (2), (-)-drimenol (3), (-)-uvidin C (4) and (-)-epi-albrassitriol (5).