21142-67-6

Basic information

• Product Name: colletodiol
• Synonyms: colletodiol;(3E,6R,9E,11R,12R,14R)-11,12-Dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione
• CAS NO: 21142-67-6
• Molecular Formula: C14H20O6
• Molecular Weight: 284.3
• Mol File: 21142-67-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: colletodiol(CAS DataBase Reference)
• NIST Chemistry Reference: colletodiol(21142-67-6)
• EPA Substance Registry System: colletodiol(21142-67-6)

Safety Data

• Hazardous Substances Data: 21142-67-6(Hazardous Substances Data)

Usage

Description

Colletodiol is a fungal metabolite derived from Chaetomium funicola and D. grovesii, known for its immunosuppressant and antiviral properties. It exhibits inhibitory effects on the proliferation of isolated mouse splenocytes and influenza A viral replication in HeLa-IAV-Luc cells. Colletodiol is also utilized in the synthesis of Grahamimycin A and colletol.

Uses

Used in Pharmaceutical Industry:
Colletodiol is used as an antiviral agent for its ability to inhibit influenza A viral replication in HeLa-IAV-Luc cells, making it a potential candidate for the development of antiviral treatments.
Used in Immunosuppressive Applications:
Colletodiol is used as an immunosuppressant due to its ability to inhibit concanavalin Aor LPS-induced proliferation of isolated mouse splenocytes, with IC50s of 12 and 5 μg/ml, respectively. This property makes it a valuable compound for the development of immunosuppressive therapies.
Used in Chemical Synthesis:
Colletodiol is used as a key intermediate in the synthesis of Grahamimycin A and colletol, which are important compounds with potential pharmaceutical applications.

Upstream product

• 133463-60-2 (E)-(4R,5R,7R)-4,5-Dihydroxy-7-((E)-(S)-5-hydroxy-hex-2-enoyloxy)-oct-2-enoic acid 
• 91273-95-9 (3E,6R,9E,11R,12R,14R)-11,12-(isopropylidenedioxy)-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione 
• 91273-95-9 (3E,6R,9E,11R,12R,14RS)-11,12-isopropylidenedioxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione 
• 50376-39-1 (6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione 
• 485323-92-0 (2E,4E)-(R)-7-(tert-Butyl-dimethyl-silanyloxy)-octa-2,4-dienoic acid methyl ester 
• 865716-47-8 acetic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-but-3-enyl ester 
• 865716-49-0 (E)-(R)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-oct-2-enoic acid methyl ester 
• 64584-92-5 (R)-pent-4-en-2-ol 
• 133522-13-1 (5R,2E)-5-(tert-butyl-dimethyl-silyloxy)-hex-2-enoic acid 
• 116773-95-6 (R)-4-<(tert-butyldimethylsilyl)oxy>-1-pentene 
• 116908-88-4 (2E,4R,5R,7R,10E,13R)-13-hydroxy-4,5-(isopropylidenedioxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid 
• 485323-89-5 (E)-3-[(4R,5R)-5-((R)-2-Hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester 
• 485323-93-1 (4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester 
• 485323-94-2 (E)-(R)-5-Hydroxy-hex-2-enoic acid (R)-2-[(4R,5R)-5-((E)-2-methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methyl-ethyl ester 

Downstream Products

• 74838-13-4 (-)-grahamimycin A₁ 
• 50376-39-1 (6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione 
• 50376-40-4 (-)-colletol 

Relevant articles and documents

A short and enantioselective synthesis of colletodiol

A 12-step enantioselective synthesis of colletodiol has been achieved using a cross-coupling metathesis and a Sharpless dihydroxylation as the key steps. Georg Thieme Verlag Stuttgart.

Biosynthesis of colletodiol and related polyketide macrodiolides in Cytospora sp. ATCC 20502: Synthesis and metabolism of advanced intermediates

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Formal total synthesis of grahamimycin A1

(S)-t-Butyldimethylsiloxy-2-hexenoic acid and its (R)-isomer were prepared from (S)- and (R)-3-hydroxybutanoic acid esters, respectively. Condensation of the both isomers with 2-(p-toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-4,5-dimethylmethylenedioxyoctan