1042952-07-7Relevant academic research and scientific papers
Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-nangustine
Kokas, Okanya J.,Banwell, Martin G.,Willis, Anthony C.
, p. 6444 - 6451 (2008/09/21)
The synthesis of (+)-nangustine [(+)-2] has been achieved, for the first time, using the enantiomerically pure cis-1,2-dihydrocatechol 3 as starting material. The latter compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of chlorobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 3 is available by related means, the present work also represents a formal total synthesis of the montanine alkaloid (-)-nangustine [(-)-2]. Single-crystal X-ray analyses of compounds 13 and (+)-2 are reported.
