Side Chain Structural Requirement for Utilization of Sterols by the Silkworm for Growth and Development. Non-stereoselective Utilization of the 24-Stereoisomeric Pairs of 24-Alkylsterols

Abstract

Four C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22R) or (22S)-Δ^23Z steroid derivatives (11 and 12). These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol. All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.