958885-86-4

Basic information

• Product Name: 12-Hydroxy-8(17),13-labdadien-16,15-olide
• Synonyms: 12-Hydroxy-8(17),13-labdadien-16,15-olide;Epivitexolide D
• CAS NO: 958885-86-4
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318
• Mol File: 958885-86-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 12-Hydroxy-8(17),13-labdadien-16,15-olide(CAS DataBase Reference)
• NIST Chemistry Reference: 12-Hydroxy-8(17),13-labdadien-16,15-olide(958885-86-4)
• EPA Substance Registry System: 12-Hydroxy-8(17),13-labdadien-16,15-olide(958885-86-4)

Safety Data

• Hazardous Substances Data: 958885-86-4(Hazardous Substances Data)

Usage

General Description

12-Hydroxy-8(17),13-labdadien-16,15-olide is a natural chemical compound belonging to the labdane diterpene class. It is commonly found in various plant species and possesses a wide range of biological activities. Studies have shown that this compound exhibits anti-inflammatory, anti-tumor, and anti-fungal properties, making it a potential candidate for the development of new pharmaceutical drugs. Its unique structure and bioactivity make it an intriguing target for further research in the fields of pharmacology and medicinal chemistry. Overall, 12-Hydroxy-8(17),13-labdadien-16,15-olide represents a promising natural product with potential therapeutic applications.

Upstream product

• 909794-72-5 (R)-1-(2-(triisopropylsilyloxy)furan-3-yl)-2-((1S,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)ethanol 
• 3243-36-5 (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde 
• 190264-38-1 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide 
• 564-20-5 (3aR)-(+)-sclareolide 
• 434284-14-7 N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 

Downstream Products

• 61597-55-5 (5S,9S,10S)-15,16-epoxy-12-hydroxy-labda-8⁽¹⁷⁾-13⁽¹⁶⁾,14-triene 

Relevant articles and documents

Lewis Acid-Catalyzed Stereoselective α-Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides

The stereoselective α-addition to cyclic dienol silanes has rarely been exploited, in contrast to the well-studied γ-addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α-addition of 2-trimetylsiloxy furan to optically pure aldehydes in water-containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural products: vitexolide D, curcucomosin C, villosin, chinensine C, (+)-coronarin E and (E)-labda-7,11,13-trien-16,15-olid.

Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B

Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.