41429-52-1

Usage

Chemical Description

(+)-Norpatchoulenol is a natural product with a bicyclic structure, while (+)-camphor-10-sulphonic acid is a chiral starting material.

InChI:InChI=1/C14H22O/c1-12(2)10-6-8-13(3)11(9-10)5-4-7-14(12,13)15/h4-5,10-11,15H,6-9H2,1-3H3/t10-,11-,13+,14+/m0/s1

Upstream product

• 77646-42-5 (1R,4S,6S)-6-((S)-1-Hydroxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 77584-07-7 (1R,4S,6S)-6-((S)-1-Hydroxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 62731-83-3 1,5,5-trimethyl-6-oxobicyclo<2.2.2>octane-2-endo-2-carbaldehyde 
• 62731-83-3 (1R,2R,4S)-1,5,5-Trimethyl-6-oxo-bicyclo[2.2.2]octane-2-carbaldehyde 
• 130852-86-7 (1S,4R,6R)-6-((R)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 91997-91-0 (1S,4R,4aR,6S,8aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-8a,9,9-trimethyl-octahydro-1,6-methano-naphthalen-1-ol 
• 57576-18-8 (+/-)-hydroxy patchouli alcohol 
• 57576-19-9 (1S,4R,4aR,6S,8aR)-1-Hydroxy-8a,9,9-trimethyl-decahydro-1,6-methano-naphthalene-4-carboxylic acid 
• 77584-08-8 (1S,4R,6R)-6-((R)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 130852-84-5 (1S,2R,4R)-1,5,5-Trimethyl-6-oxo-bicyclo[2.2.2]octane-2-carbaldehyde 
• 130740-90-8 (1S,4R)-6-[1-Methoxy-meth-(Z)-ylidene]-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 130852-87-8 (1S,4R,6R)-6-((S)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 

Relevant academic research and scientific papers

The Total Synthesis of (+)-Norpatchoulenol: Trapping of a Non-enolizable 1,3-Diketone Intermediate with a Wittig Reagent

A short total synthesis of (+)-norpatchoulenol (1) has been accomplished from (+)-camphor-10-sulphonic acid (2) involving, as a key step, the trapping of a non-enolizable 1,3-diketone intermediate with a Wittig reagent.

STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-NORPATCHOULENOL AND TWO METABOLITES OF PATCHOULI ALCOHOL, (+/-)-HYDROXY PATCHOULI ALCOHOL AND THE CORRESPONDING (+/-)-CARBOXYLIC ACID

The first total synthesis of the two biooxidation products of patchouli alcohol (2), (+/-)-hydroxy patchouli alcohol (3) and the corresponding (+/-)-carboxylic acid 4, has been achieved in highly stereocontrolled manners.Synthesis of (+/-)-norpatchoulenol (1), the real odoriferous substance of patchouli oil, has been accomplished by the biogenetic route via (+/-)-3 and (+/-)-4.

STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-HYDROXY PATCHOULI ALCOHOL AND THE CORRESPONDING (+/-)-CARBOXYLIC ACID, METABOLITES OF PATCHOULI ALCOHOL, AND (+/-)-NORPATCHOULENOL

The first total synthesis of (+/-)-hydroxy patchouli alcohol (3) and the corresponding (+/-)-carboxylic acid 4, the biooxidation products of patchouli alcohol (2) has been achieved. (+/-)-Norpatchoulenol (1) has also been synthesized by the biogenetic route via 3 and 4.