Synthesis of racemic and each enantiomer of 3-methylnonacosanol, a new plant growth regulator from Lowsonia inermis

An efficient synthesis of the title compound I in racemic and enantiomeric forms has been developed starting from 10-undecenoic acid. For the enantiom eric synthesis, a lipase catalyzed acylation strategy was employed to prepa re the required methyl branched chiron which was subsequently derivatized t o give the enantiomers of I. The plant growth regulatory (PGR) assay of I, carried out with hypocotyl cuttings of French beans (Phaseolus vulgaris L.) in Steinberg's nutrient medium revealed appreciable activity at a concentr ation of 2.5 ppm. The PGR activities of the compound both in racemic and en antiomeric forms were better than 1-triacontanol, the enantiomer, (S)-I bei ng the best test candidate. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.