Diterpenoids

Isolation, Chemical, and Biotransformation Routes of Labdane-type Diterpenes

“…In 2007, Pilar Basabe and co-workers reported the synthesis of γ-acetoxybutenolide (+)-lagerstronolide ( 127 ) from (−)-sclareol, in an overall yield of 10% (Scheme ) . (+)-Lagerstronolide is a molecule isolated from the plant Lagerstreomia lancasteri, which contains a unit of γ-hydroxybutenolide. , This functional group is present in diverse derivatives with important biologic activities, such as luffolide (anti-inflammatory activity), dysidiolide (which is an inhibitor of the cdc25A protein phosphatase), and its analogues (which have antitumor properties) . Although the route to 127 involves 12 reaction steps, as shown in Scheme , it is very elegant.…”

Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions

“…Diterpenes belonging to the phyllocladane 114 and kaurane 115 families (Figure 41) are widespread in nature. 85 Some representatives such as steviol, stevioside, hibaol, enmein, cafestol, atractyligenin, etc., display important biological properties 86 and, for example, the ent-kaurane group plays a fundamental role as biosynthetic precursor of the plant growth hormone gibberelins. 87 Inspection of phyllocladane and kaurane molecules reveals the presence of a trans-anti-trans perhydrophenanthrene system in 114 and a trans-anti-cis one in 115.…”

Structure of dimethyl (±)-1,2,3,4,4aα,4b,9,10-octahydro-6,7-bis(trimethylsilyl)-2β,10aβ-ethanophenanthrene-12,12-dicarboxylate

“…Introduction. Kaurane and phyllocladane are two families of naturally occurring tetracyclic diterpenes exhibiting very important biological activities (Hanson, 1988). They have very close structural features with a bicyclo[3.2.1]octane arrangement of CD rings and a spiro BD ring junction in common; the only difference in structure arises from the stereochemistry of the BC ring junction: cis for the kaurane, trans for the phyllocladane.…”