96910-70-2

Upstream product

• 37841-91-1 (+)-isovelleral 
• 82351-48-2 ethyl trans-4,4-dimethyl-6-oxo-2-hexenoate 
• 5497-67-6 2,2-dimethyl-4-pentenal 

Downstream Products

• 395664-47-8 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (1aS,3aS,6aS,6bR)-1a-formyl-5,5,6b-trimethyl-1,1a,3a,4,5,6,6a,6b-octahydro-cyclopropa[e]inden-2-ylmethyl ester 
• 679000-71-6 (2R,3S)-3-Phenyl-1-oxa-4-aza-spiro[4.5]decane-2,4-dicarboxylic acid 2-((1aS,3aS,6aS,6bR)-1a-formyl-5,5,6b-trimethyl-1,1a,3a,4,5,6,6a,6b-octahydro-cyclopropa[e]inden-2-ylmethyl) ester 4-(2,2,2-trichloro-ethyl) ester 
• 37841-91-1 (+)-isovelleral 

Relevant academic research and scientific papers

TRANSFORMATION OF ISOVELLERAL BY THE PARASITIC FUNGUS CALCARISPORIUM ARBUSCULA

The fungus Calcarisporium arbuscula, a parasite in fruit bodies of species of Russlaceae, resists high concentrations of the antifungal sesquiterpene isovelleral, a suggested defence compound formed enzymatically in many of ist hosts as a response to injury.This insensitivity is suggested to be due to the ability of C. arbuscula to transform isovelleral primarily to the reduced derivative isovellerol.Another fungicolous fungus, Amblyosporium spongiosum, which grows on the surface of the fruit bodies of many Basidiomycetes (including Russulaceae), also tolerates high concentrations of isovelleral, but does not transform the compound to the extent of more than a few per cent.Key Words Index - Calcarisporium arbuscula, Amblyosporium spongiosum; parasitic fungi; Russulaceae; isovelleral; isovellerol.

A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products

The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are 1) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, 2) the utility of a key 1,2-cyclobutanediol intermediate to serve as a precursor to each natural product class, and 3) a direct chemical conversion of a protoilludane to a marasmane through serendipitous ring contraction, which provides experimental support for their proposed biosynthetic relationships.