15798-13-7Relevant articles and documents
Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae)
Iwamoto, Manabu,Ohtsu, Hironori,Tokuda, Harukuni,Nishino, Hoyoku,Matsunaga, Shunyo,Tanaka, Reiko
, p. 1911 - 1921 (2001)
Three new labdane-type diterpenoids, labda-8(17), 13-dien-15,2R-olid-19-oic acid (1), 12S-hydroxylabda-8(17),13(16),14-trien-19-oic acid (2) and 13-ethoxylabda-8(17), 11,14-trien-19-oic acid (3), along with known diterpenoids, trans-communic acid (4), totarol (5), 12-methoxyabieta-8,11,13-trien-11-ol (6), and 7α,8α-epoxy-6α-hydroxyabieta-9(11),13-dien-12-one (7) were isolated from the stem bark of Thuja standishii. The structures of 1-3 were established by spectroscopic methods and chemical conversion. These compounds together with standishii. (8), 12-hydroxy-6,7-seco-abieta-8,1,13-trien-6,7-dial (9) and 6α-hydroxysugiol (10) were tested for their inhibitory efects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), as a test for potential cancer chemopreventive agents. Compound 10 showed strong inhibitory effect on EBV-EA induction. In addition, 15-oxolabda-8(17),11Z,13E-trien-19-oic acid (11) was found to exhibit the anti-tumor promoting activity in two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene and TPA. Copyright
Syntheses and structural confirmations of members of a heterocycle- containing family of labdane diterpenoids
MacK, Daniel J.,Njardarson, Jon T.
supporting information, p. 1543 - 1547 (2013/04/23)
Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper-catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1-5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent-controlled oxidation and 1,3-diene isomerization results are also presented. Copyright
Synthesis of phenol abietane diterpenes based on the oxidative radical cyclization utilizing the Mn(OAc)3/Ac2O system
Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Cabrera, Eduardo,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Lachkar, Mohammed,Messouri, Ibtissam
, p. 2425 - 2429 (2008/03/27)
A new route to phenol abietane diterpenes from trans-communic acid is reported. The key step is the transformation of a β-ketoester into the corresponding O-acetylsalicilate, via a manganese(III)-based oxidative free-radical cyclization carried out in Ac2O. Utilizing this, the first synthesis of (-)-sugikurojin A has been achieved. The immunosuppressor 19-hydroxyferruginol has also been synthesized. Georg Thieme Verlag Stuttgart.
Chemistry of the Podocarpaceae. LVI Resin Acids from Phyllocladus trichomanoides
Cambie, Richard C.,Grigor, Bruce A.,Mee-Ing, Tiong
, p. 1073 - 1078 (2007/10/02)
Five diterpenoid acids of the labdane type have been isolated from the bled resin of Phyllocladus trichomanoides by reversed-phase h.p.l.c.