MICROBIOLOGICAL HYDROXYLATION OF 1-BENZOYL-TRANS-DECAHYDROQUINOLINE . DETERMINATION OF STRUCTURE STEREOCHEMISTRY AND ABSOLUTE CONFIGURATION OF PRODUCTS

Microbiological hydroxylation of (±)-1-benzoyl-trans-decahydroquinoline [(±)-2] with Sporotrichum sulfuresems has been shown to give (4aS,5S,8aR)-1-benzoyl-trans-decahydroquinolin-5-ol (3), (±)-1-benzoylirans- decahydroquinolin-6-ol (4), and (4aS,7S,8aS)-1-benzoyl-trans-decahydroquinolin-7-ol (5) in a total yield of 80-90%. Under the same conditions hydroxylation of (+)-2 gave optically pure (+)-5 and (4aS,6S,8aS)-1-benzoyl- trans-decahydroquinolin-6-ol [(+)-4] in a ratio of 35:65. Hydroxylation of (-)-2 gave optically pure (-)-3 and (4aR,6R,8aR)-1-benzoyl-trans-decahydroquinolin-6-ol [(-)-4] in a ratio of 87:13. Various chemical modifications of these products were carried out in order to determine their structures and stereochemistry and included the conversions of 3, (+)-5, and (+)-4 into (4aS,8aS)-trans-decahydroquinolin-5-one (24), (4aS,8aS)-trans-decahydroquinolin-7-one (26), and (4aS,8aS)-trans-decahydroquinolin-6-one (25), respectively. Application of the octant rule to the optical rotatory dispersion curves of the latter compounds allowed assignment of absolute configurations to the hydroxylation products. The absolute configurations of the parent molecules, (-)-trans-decahydroquinoline [(-)-1] and (+)-trans-decahydroquinoline [(+)-1], can be assigned as (4aR,8aS)-trans-decahydroquinoline and (4aS,8aR)-trans-decahydroquinoline, respectively. © 1968, American Chemical Society. All rights reserved.