Incubation of (S)-[1-2H1]geranylgeranyl pyrophosphate (1b) with an enzyme extract from castor bean (Ricinus communis L.) seedlings produced (E)-[16-2H1]-ent-sandarocopimaradiene (3b); thus, the SN′ cyclization of the intermediate copalyl pyrophosphate (2b) occurs with anti-stereochemistry.
K. A. Drengler and R. M. Coates, J. Chem. Soc., Chem. Commun., 1980, 856 DOI: 10.1039/C39800000856
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