50376-40-4

Basic information

• Product Name: (-)-Colletol
• Synonyms: (-)-Colletol;(3E,6R,9E,12S,14R)-12-Hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione;Colletol
• CAS NO: 50376-40-4
• Molecular Formula: C14H20O5
• Molecular Weight: 268.3056
• Mol File: 50376-40-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Colletol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Colletol(50376-40-4)
• EPA Substance Registry System: (-)-Colletol(50376-40-4)

Safety Data

• Hazardous Substances Data: 50376-40-4(Hazardous Substances Data)

Upstream product

• 136444-79-6 (2E,5S,7R)-Ethyl 10-(diethoxyphosphinyl)-5-(tert-butyldimethylsiloxy)-7-methyl-9-oxo-8-oxa-2-decenethioate 
• 136444-79-6 (2Z,5S,7R)-Ethyl 10-(diethoxyphosphinyl)-5-(tert-butyldimethylsiloxy)-7-methyl-9-oxo-8-oxa-2-decenethioate 
• 136444-78-5 (Σ,6R)-9-(Diethoxyphosphinyl)-8-oxo-6-methyl-4-(tert-butyldimethylsiloxy)-7-oxa-1-nonene 
• 136444-81-0 (2E,5S,7R,10E,13R)-Ethyl 13-hydroxy-5-(tert-butyldimethylsiloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienethioate 
• 136444-82-1 (2E,5S,7R,10E,13R) 13-Hydroxy-5-(tert-butyldimethylsiloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid 
• 136444-76-3 (((4S,6S)-6-(benzyloxy)hept-1-en-4-yl)oxy)(tert-butyldimethylsilane) 
• 136444-77-4 (4S,6S)-4-(tert-Butyldimethylsiloxy)-6-hydroxy-1-heptene 
• 136521-65-8 (4S,6S)-4-Hydroxy-6-(benzyloxy)-1-heptene 
• 154457-21-3 (E)-(5S,7R)-7-[(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-hex-2-enoyloxy]-5-methoxymethoxy-oct-2-enoic acid allyl ester 
• 154457-22-4 (2E,5S,7R)-7-[(2E,5R)-5-hydroxyhex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoic acid 
• 154457-17-7 (E)-3-{(2R,3R)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-oxiranyl}-acrylic acid ethyl ester 
• 154457-20-2 (E)-(5S,7R)-7-Hydroxy-5-methoxymethoxy-oct-2-enoic acid allyl ester 
• 154457-18-8 (E)-(5S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-oct-2-enoic acid ethyl ester 
• 154457-19-9 (E)-(5S,7R)-7-Hydroxy-5-methoxymethoxy-oct-2-enoic acid ethyl ester 

Relevant articles and documents

First 'Chiron Approach' based convergent synthesis of (-)-Colletol from D-xylose

A protocol, based on 'chiron approach', for the synthesis of (-)-colletol is described, which involves the coupling of two appropriately protected hydroxy acids that are derived from D-xylose and macrolactonisation of seco-acid under Yamaguchi conditions.

Two approaches for efficient synthesis of (-)-colletol

The synthesis of (-)-colletol was achieved from (R)-pent-4-en-2-ol by using enantioselective allyltitanations to control the stereogenic centers at C5 and cross-metathesis, ring-closing metathesis reactions to control the configuration of the double bonds.

Stereoselective total synthesis of (-)-colletol by Prins cyclisation

A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mit

Enantioselective syntheses of colletodiol, colletol, and grahamimycin A.

[reaction: see text] The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

Enantioselective synthesis of the unsymmetrical bis(lactone) (-)- (3E,6R,9E,12S,14R)-colletol induced by chiral sulfoxides and an approach to (+)-colletodiol by asymmetric hydroxylation of an α,β-hydroxy lactone

A general synthetic strategy towards the two bis(lactones) (-)colletol (1) and (+)-colletodiol (2) is described. A common intermediate in this synthesis is the 6-membered hydroxy lactone (+)-(3R,5R)-3-hydroxy-5- hexanolide (6), readily prepared by stereos

Chiral Synthesis of (-)-Colletol Based on Palladium-Catalyzed Reductive Cleavage of Alkenyloxiranes with Formic Acid

Total synthesis of (-)-colletol was achieved using palladium-catalyzed hydrogenolysis of optically active (E)-4,5-epoxy-2-alkenoates to (E)-5-hydroxy-2-alkenoates with formic acid as a key step for preparation of the intermediate hydroxy ester segments.

Total Synthesis of (-)-Colletol

The first total synthesis of the unsymmetrical bis-macrolide (-)-colletol is described.The synthesis involves a Lewis acid mediated addition of triphenylallylstannane to aldehyde 14 to set the C12 stereochemistry.The penultimate step utilized m