Penicillium concavo-rugulosum

From cultures of a mold, Penicillium concavo-rugulosum, two new alkaloids as well as chanoclavine-I (4) were isolated by routine procedures (9). The new compounds were called rugulovasine-A (C16H16N202 mp 138° [a]D 0° in pyridine hydrochloride, mp 225° oxalate, mp 224°) and rugulovasine-B (C16H16N202 amorphous [ ]D 0° in pyridine hydrochloride, mp 187° oxalate, mp 217°). They proved to be closely related to each other since they were easily interconvertible when heated in alcohol solution. 

Polar groups on the substrate molecule can facilitate hydroxyladon of nonactivated positions, and the cyclohexane derivative (18) is regio- and stereo-selectively hydroxylated in 71% yield by Penicillium concavo-rugulosum (equation 6). ... 

Cycloclavine (30), from Ipomoea hildebrandtii, contains a cyclopropane ring, as established by an Z-ray analysis of its methobromide salt. The rugulovasines A and B (31) are optical isomers from Penicillium concavo-rugulosum. Their structures are supported by an analysis of their n.m.r. spectra and by the cooccurrence of chanoclavine in the same culture. 

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