Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade
An electrochemical ODI-[5+2] cascade reaction was developed which enables the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. By combining a directed retro-aldol/aldol process, a [2,3]-sigmatropic rearr
First synthesis of cytotoxic 8,9-secokaurene diterpenoids. An enantioselective route to (-)-O-methylshikoccin and (+)- O-methylepoxyshikoccin
A practical route for the total synthesis of 8,9-secokaurene diterpenes is described. The central step is the 3.3]sigmatropic rearrangement of spirocyclic intermediates such as 35, 40, and 41. All three compounds must necessarily respond identically to pr
Paquette, Leo A.,Backhaus, Dirk,Braun, Ralf,Underiner, Ted L.,Fuchs, Klaus
p. 9662 - 9671
(2007/10/03)
Direct asymmetric entry into the cytotoxic 8,9-secokaurene diterpenoids. Total synthesis of (-)-O-methylshikoccin and (+)-O-(methylepoxy)shikoccin
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Paquette, Leo A.,Backhaus, Dirk,Braun, Ralf
p. 11990 - 11991
(2007/10/03)
Terpenoids. XLVIII. New Diterpenoids from Rabdosia shikokiana var. occidentalis
Five new kaurene-type diterpenoids, shikoccin (1), O-methylshikoccin (2), epoxyshikoccin (3), O-methylepoxyshikoccin (4) and shikoccidin (5) were isolated from Rabdosia shikokiana var. occidentalis.All these compounds except for 5 possess a hitherto unknown 8,9-seco-ent-kaurene skeleton.Keywords-Rabdosia shikokiana; diterpenoid; shikoccin; shikoccidin; ent-kaurene; Labiatae
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