Caryophyllane, Humulane, Africane, Illudalane, Protoilludane, Hirsutane, Vellerane, Pentalane, Senoxydane

11 Caryophyllane, Humulane, Africane, Illudalane, Protoilludane, Hirsutane, Vellerane, Pentalane, Senoxydane 

A full paper on the determination of the structure and absolute configuration of the two piscicidal sesquiterpenoids buddledins A (238) and B (239) has now appeared.Buddledin A has also been isolated from another Buddleja species.In addition, the structures of buddledins C (240), D (241), and E (242) have been determined and toxicity tests have shown that the latter two are not piscicidal. Another interesting oxygenated caryophyllene derivative is lych-nopholic acid (243) from Lychnophora affinis Gardn. The structure of this compound has been elucidated by a combination of n.m.r. and X-ray spectral studies. 

The nor-ketone rudbeckianone (244) has been identified in Rudbeckia lacini-ata A very interesting new sesquiterpenoid ketone, (+)-bicyclohumulenone (245), has been isolated from the leafy liverwort Plagiochila acanthophylla subsp. japonica The structure and absolute stereochemistry of this compound were ascertained by X-ray crystallographic analysis of the mono-p-bromobenzoate of the derived triol (246). This ketone co-occurs with the two enantiomeric sesquiterpenoids (-)-maalioxide (247) and (+)-cyclocolerenone (248). 

Complete details of the acid-catalysed rearrangement of humulene 1,2-epox-ide (249) have now been presented. With 1.8M-sulphuric acid in acetone at 0 °C for 30 min the sole product is the previously known tricyclic diol (250). After an extended period this diol gives rise to five other identified products. 

Yoshida, J. Nobuhara, N. Fujii, and T. Okuda, Chem. Pharm. Bull., 1978, 26, 2543. 

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