Total synthesis of viridiofungin A

Abstract

Viridiofungin A, a member of amino alkyl citrate antibiotics from Trichoderma viride, was enantioselectively synthesized in naturally occurring form for the first time, employing regio- and stereoselective opening of the chiral glycidate with vinylmagnesium bromide and alkene cross metathesis of the citric acid core and hexadec-15-en-8-one as key steps.

Secondary metabolites from species of the biocontrol agent Trichoderma

“…The first synthesis of Me 3 -43 was achieved by Esumi et al (1998) allowing for the designation of the relative and absolute configuration of 43. A modified synthesis of 43 by acidic hydrolysis of the tri-tertbutyl ester derivative (t-Bu) 3 -43 was reported in 2005 (Morokuma et al 2005).…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Alkene-alkene CM were used in synthesis toward viridiofungin A [1226], 2,7-diaminosuberic acid derivatives [1227], radicicol and pochonin C [1122], (+)-cyanthiwigin U [1228], apoptolidinone (Eq. (225)) [1229], the C9-C16 segment of ambruticin [1230], (−)-lemonomycin [1231], aureothin and Nacylaureothamine [61], the C22-C36 subunit of halichondrin B [654], the A ring of bryostatin analogs [1232], misakinolide A [1233], ␣-C-glucosyl serine and alanine [1234], the C26-C40 subunit of spirastrellolide [941], glutamic acid side chain homologues [1235], discodermolide analogues [1236], the C6-C21 segment of amphidinolide E [270], fraxinellone limonoids [1237], (+)-phomopsolide C [1167], pinnaic acid and halichlorine [1238], sphingosines [1239], mollugin and microphyllaquinone [1240], mucocin [645], (+)-anatoxin-a [1241], colletodiol [1242], toward paulitin [1243], tashiromine [1244], (−)-nupharamine [1245], octalactin lactone [1246], 3-hydroxy-4-methyl-2-tetradecyl-4-butenolide [945], 5,5-dimethylproline [1247], xenovenine and indolizine 209D [1248] and bengamides [1249].…”

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

“…In addition to the total syntheses presented in this review, we also achieved the syntheses of a variety of biologically active natural products with structural challenges such as febrifugine, 114) viridiofungin A, 115) trachyspic acid, 116) cinatrin C 1 , 117) β-erythroidine, 118) NW-G01, 119) inthomycins A-C, 120) englerin A, 121) ophiodilactones A and B, 122) and marinomycin A. 123) The strategies and methodologies we have developed are of great potential value in synthetic organic chemistry as well as pharmaceutical research.…”