This review provides the first overview on the isolation and structure elucidation of a class of isopimaric diterpenes: virescenols. An important part of this review deals with the structural modifications of virescenols leading to several different natural product frameworks.
FassiB. (1951) Prove preliminari sull'azione antibiotica di Oospora virescens (Link) Wallr. e sulle sue possibili applicazioni pratiche. Annali dell'Accademia di Agricoltura di Torino, 93, 29–48.
2.
Cagnoli BellavitaN, CeccherelliP, RibaldiM, BaskevitchZ, PolonskyJ. (1967) Metaboliti della Oospora virescens (Link) Wallr. Virescenolo A. Gazzetta Chimica Italiana, 97, 1344–1346.
3.
Cagnoli BellavitaN, CeccherelliP, RibaldiM, BaskevitchZ, PolonskyJ. (1967) Metaboliti della Oospora virescens (Link) Wallr. Virescenolo B. Gazzetta Chimica Italiana, 97, 1624–1625.
4.
PolonskyJ, BaskevitchZ, Cagnoli BellavitaN, CeccherelliP. (1968) The structures of Virescenol A and B, Metabolites of Oospora virescens (Link) Wallr. Chemical Communications, 1404–1405.
5.
PolonskyJ, BaskevitchZ, Cagnoli BellavitaN, CeccherelliP. (1970) Structures des virescenols A et B, métabolites d'Oospora virescens (Link) Wallr. Bulletin de la Société Chimique de France, 1912–1918.
6.
Cagnoli BellavitaN, CeccherelliP, RibaldiM, PolonskyJ, BaskevitchZ. (1969) Virescenoside A e Virescenoside B: nuovi altrosidi metaboliti dell'Oospora virescens (Link) Wallr. Gazzetta Chimica Italiana, 99, 1354–1363.
7.
CeccherelliP, Cagnoli BellavitaN, PolonskyJ, BaskevitchZ, RibaldiM. (1977) The structures of Virescenoside E and L, new metabolites of Acremonium luzulae (Fukel) Gams. Gazzetta Chimica Italiana, 107, 51–53.
8.
Cagnoli BellavitaN, CeccherelliP, RibaldiM, PolonskyJ, Baskevitch-VaronZ, VarenneJ. (1977) Structures of Virescenosides D and H, new metabolites of Acremonium luzulae (Fukel) Gams. Journal of the Chemical Society, Perkin Transactions 1, 351–354.
9.
CeccherelliP, Cagnoli BellavitaN, PolonskyJ, BaskevitchZ. (1973) Structures des virescenosides F et G, noveaux metabolites de Oospora virescens (link) Wallr. Tetrahedron, 29, 449–454.
10.
AfiyatullovSSh, KalinovskyAI, KuznetsovaTA, PivkinMV, ProkofevaNG, DmitrenokPV, ElyakovGB. (2004) New glycosides of the fungus Acremonium striatisporium isolated from a sea cucumber. Journal of Natural Products, 67, 1047–1051.
11.
AfiyatullovSSh, KalinovskyAI, KuznetsovaTA, IsakovVV, PivkinMV, DmitrenokPV, ElyakovGB. (2002) New diterpene glycosides of the fungus Acremonium striatisporium isolated from a sea cucumber. Journal of Natural Products, 65, 641–644.
12.
AfiyatullovSSh, KalinovskyAI, PivkinMV, DmitrenokPS, KuznetsovaTA. (2006) New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber. Natural Product Research, 20, 902–908.
13.
Cagnoli BellavitaN, CeccherelliP, MarianiR, PolonskyJ, BaskevitchZ. (1970) Structure du virescenoside C, nouveau métabolite de Oospora virescens (Link) Wallr. European Journal Biochemistry, 15, 356–359.
14.
Cagnoli BellavitaN, CeccherelliP, CuriniM, MadruzzaGF, RibaldiM. (1982) Isopimara-7,15-dien-19-ol: a new diterpenoid from Acremonium luzulae (Fukel) Gams. Journal of Chemical Research (S), 254.
15.
Cagnoli BellavitaN, CeccherelliP, CuriniM, SpagnoliN, RibaldiM. (1980) 19-Nor-isopima-7,15-dien-3-one: a new norditerpenoid from Acremonium luzulae (Fukel) Gams. Journal of Chemical Research (S), 276.
16.
GrantPK, HuntrakulC, SheppardDRJ. (1967) Diterpenes of Dacrydium bidwillii. Australian Journal of Chemistry, 20, 969–972;
17.
AppletonRA, RoeraadeJ. (1969) 18-Norisopimara-4(19),7,15-triene: a norditerpenoid from Dacrydium biforme. Chemical Communications, 1407.
18.
AfiyatullovSSh, KuznetsovaTA, IsakovVV, PivkinMV, ProkofevaNG, ElyakovGB. (2000) New diterpenic altrosides of the fungus Acremonium stritisporium isolated from a sea cucumber. Journal of Natural Products, 63, 848–850.
19.
AfiyatullovSSh, KuznetsovaTA, IsakovVV, PivkinMV, ProkofevaNG, ElyakovGB. (2005) New diterpenic altrosides of the fungus Acremonium stritisporium isolated from a sea cucumber. Journal of Natural Products, 68, 1308.
20.
RichtmyerNK. (1962) In Methods in Carbohydrate Chemistry, WhistlerRL, WolfromML (Eds), Academic Press, 107.
21.
Cagnoli BellavitaN (1974) Glycoside metabolites of Oospora virescens Wallr. fungus. US Patent 3855067.
22.
PolonskyJ, BaskevitchZ, Cagnoli BellavitaN, CeccherelliP, BuckwalterBL, WenkertE. (1972) Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XI. Biosynthesis of the virescenosides. Journal of the American Chemical Society, 94, 4369–4370.
23.
NicholasHJ. (1967) In Biogenesis of Natural Compounds.BernfeldP (Ed). Pergamon Press, New York, N.Y.
24.
PolonskyJ, LukacsG, Cagnoli BellavitaN, CeccherelliP. (1975) Application du couplage 13C-13C a la determination de l'origine biogenetique des substituants en C-4 des virescenols A et B. Tetrahedron Letters, 481–484.
25.
CaneDE, HaslerH, MaternaJ, Cagnoli BellavitaN, CeccherelliP, MadruzzaGF, PolonskyJ. (1981) 1H-NMR Determination of the stereochemistry of an allylic displacement in the biosynthesis of virescenol B. Chemical Communications, 280–282.
26.
CaneDE, MurthyPPN. (1977) Application of deuterium magnetic resonance to biosynthetic studies. 2. Rosenonolactone biosynthesis and stereochemistry of a biological SN2′ reaction. Journal of the American Chemical Society, 99, 8327–8329;
27.
DrenglerKA, CoatesRM. (1980) Stereochemistry of the SN’ cyclization in the biosynthesis of ent-sandarocopimaradiene with enzyme extracts from seedlings of Ricinus communis L. Chemical Communications, 856–857;
28.
CoatesRM, CavenderPL. (1980) Stereochemistry of the enzymic cyclization of copalyl pyrophosphate to kaurene in enzyme preparations from Marah macrocarpus. Journal of the American Chemical Society, 102, 6358–6359;
29.
EvansR, HansonJR, MulheirnLJ. (1973) Terpenoid biosynthesis. X. Incorporation of (5S)-[5-3H]mevalonic acid into gibberellic acid. Journal of the Chemical Society, Perkin Transactions 1, 753–756.
30.
CeccherelliP, CuriniM, PellicciariR, RajuMS, WenkertE. (1977) Conversion of virescenol A into virescenol B. Journal of Organic Chemistry, 42, 3438–3440.
31.
PassannantiS, PaternostroM, PiozziF, BarbagalloC. (1984) Diterpenes from the genus Amaracus. Journal of Natural Products, 47, 885–889.
32.
PalumboG, FerreriC, CaputoR. (1983) A new general synthesis of halohydrins. Tetrahedron Letters, 1307–1310.
33.
CeccherelliP, CuriniM, MarcotullioMC. (1985) 3β,19-oxidoisopimara-7,15 diene as intermediate in the conversion of virescenol B into isopimara-7,15-dien-19-ol. Journal of the Chemical Society, Perkin Transaction 1, 2173–2175.
34.
CorbettRE, SmithRAJ. (1967) Diterpenes from the volatile oil of Dacrydium colensoi. Journal of the Chemical Society, C, 300–302.
35.
CeccherelliP, CuriniM, PellicciariR, CocciaR, WenkertE. (1982) Reductions of diterpene epoxides. A partial synthesis of 8β-hydroxyisopimar-15-ene. Journal of Organic Chemistry, 47, 3587–3589.
36.
ApSimonJW. (1970) Synthesis of 7-isopimarene-18-oic acid (dihydroisopimaric acid). Chemical Communications, 83–84.
37.
CuriniM, CeccherelliP, PellicciariR, SisaniE. (1980) 7,8-isopimarenic epoxides: preparation and acid-catalysed ring cleavage. Gazzetta Chimica Italiana, 110, 621–623.
38.
CuriniM, CocciaR, CeccherelliP, HallsTDJ, PorterB, WenkertE. (1984) Carbon-carbon bond formation by the reduction of dienic esters. Journal of Organic Chemistry, 49, 2054–2056.
39.
CeccherelliP, CuriniM, PellicciariR. (1981) Conversion of isopimaradienes into the corresponding 7,8-dihydro derivatives. Gazzetta Chimica Italiana, 111, 509–510.
40.
Unpublishedresults, MarcotullioMC. (1985) α-Diazochetopimareni quail intermedi nella sintesi di prodotti naturali di interesse biologico. PhD thesis.
41.
CeccherelliP, CuriniM, TingoliM, PellicciariR. (1978) Attempts to induce the pimarane-cassane ring system transformation. Gazzetta Chimica Italiana, 108, 129–130.
42.
JohnstonJP, OvertonKH. (1973) The pimarane→cassane rearrangement. Synthesis of a potential intermediate from isopimaric acid. Journal of the Chemical Society, Perkin Transaction 1, 853–858.
43.
MeinwaldJ, CurtisGG, GassmanPG (1962) D-Norsteroids. Journal of the American Chemical Society, 84, 116–117;
44.
CavaMP, MorozE. (1962) A synthesis of D-norsteroids. Journal of the American Chemical Society, 84, 115–116;
45.
MullerG, HuyuhC, MathieuJ. (1962) Access to D-norsteroids. Bulletin de la Societe Chimique de France, 296–298.
46.
CeccherelliP, TingoliM, CuriniM, PellicciariR. (1978) The preparation of D-norsteroidal skeletal type from diterpenic precursor. Tetrahedron Letters, 3869–3870.
47.
CeccherelliP, TingoliM, CuriniM, PellicciariR. (1978) Tetracyclic diterpenoids by intramolecular C-alkylation of γ,δ-unsaturated diazo ketones. Tetrahedron Letters, 4969–4962.
48.
CeccherelliP, CuriniM, MarcotullioMC, RosatiO. (1991) Regiocontrol by the carbon-carbon double bond in the Rh2(OAc)4 mediated carbon-hydrogen insertion of α-diazo-ketones. Tetrahedron, 35, 7403–7408.
49.
CeccherelliP, CuriniM, TingoliM, PellicciariR. (1980) Acid-catalysed decomposition of β,γ-unsaturated diazo-ketones: preparation of 4,4-dimethyl-D-nor-steroidal systems from pimaradiene and sandaracopimaradiene precursors. Journal of the Chemical Society, Perkin Transaction 1, 1924–1927.
50.
WenkertE, DavisLL, BanavaraLM, SolomonMF, da SilvaRR, ShulmanS, WarnetRJ, CeccherelliP, CuriniM, PellicciariR. (1982) Cyclopentanone synthesis by intramolecular carbon-hydrogen insertion of diazo ketones. A diterpene-to-steroid skeleton conversion. Journal of Organic Chemistry, 47, 3242–3247.
51.
Ibrahim-OualiM. (2007) Recent advances in oxasteroids chemistry. Steroids, 72, 475–508;
52.
SinghH, KapoorVK, DharamP. (1979) In Progress in Medicinal Chemistry, 16, EllisGP and WestGB (Ed.) Elsevier/North Holland Biomedical Press, 37.
53.
BeerCT, GallagherTF. (1955) Excretion of estrogen metabolites by humans. I. The fate of small doses of estrone and 17β-estradiol. Journal Biological Chemistry, 214, 335–349.
54.
CeccherelliP, CuriniM, PellicciariR. (1982) The preparation of dimethyl-15-oxa steroid. Il Farmaco, 145–148.
55.
WenkertE, StrikeDP. (1962) Synthesis of 1-methyl-bicyclo[3.1.1]heptan-6-one. Jornal of Organic Chemistry, 27, 1883–1885;
56.
WibergKB, KleinGW. (1963) Base catalyzed cyclization of 2-alkyl-2-(p-tolylsulfonyloxy-methyl)cyclohexanones. Tetrahedron Letters, 1043–1045.
57.
PellicciariR, CeccherelliP, MazzamurroRL. (1975) Trasformazione dell'anello A di un diterpene in un sistema biciclo[3.2.0]eptanonico. Annali di Chimica, 65, 147–153.
58.
CeccherelliP, CuriniM, PellicciariR, WenkertE. (1982) A partial homo-Favorskii rearrangement in the diterpene series. Journal of Organic Chemistry, 47, 3172–3174.
59.
CeccherelliP, CuriniM, CocciaR, DiamantiniM. (1984) A cyclopropanol derivative a san intermediate for the preparation of A-homopimarane. Journal of the Chemical Society, Perkin Transaction 1, 1693–1695.
60.
CeccherelliP, CuriniM, PellicciariR, BaddeleyGV, RajuMS, WenkertE. (1978) Solvolysis of virescenol B 19-tosylate. Journal of Organic Chemistry, 43, 4244–4245.
61.
DjerassiC, CaisM, MitscherLA. (1959) Terpenoids XXXVII. The structure of pentacyclic diterpeni cafestol. On the absolute configuration of diterpenes and alkaloids of the phyllocladene group. Journal of the American Chemical Society, 81, 2386–2398.
62.
CeccherelliP, CuriniM, MarcotullioMC, BanavaraLM, WenkertE. (1986) Iodohydrins and tetrahydrofurans from lead tetraacetate-iodine oxidation of terpenic alcohols. Journal of Organic Chemistry, 51, 1505–1509.
63.
CeccherelliP, PellicciariR, Cagnoli BellavitaN, FringuelliR. (1975) Trasformazioni nell'anello A di diterpeni. Sintesi del 2-chetoisopimaradiene. Annali di Chimica, 65, 25–28.
64.
WenkertE, HallsTDJ, CeccherelliP, CuriniM, PellicciariR. (1981) C(15) configuration of isopimaren-15,16-diols and sandaracopimaren-15,16–diols. Journal of Organic Chemistry, 46, 3135–3137.
65.
WenkertE, RajuMS, CeccherelliP, CuriniM, TingoliM, PellicciariR. (1980) C(15) configuration of isopimaren-15,16-diols. Journal of Organic Chemistry, 45, 741–744.
