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ChemicalBook CAS DataBase List 5ALPHA-ANDROST-16-EN-3-ONE
18339-16-7

5ALPHA-ANDROST-16-EN-3-ONE synthesis

3synthesis methods

5α-Androst-16-en-3-one is a mammalian pheromone released as a volatile chemical cue in boar saliva to facilitate social and sexual interactions.   It is synthesized in boar testes and transported via the bloodstream to the salivary gland, where it is bound to a specific binding protein.

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Yield:-

Steps:

Multi-step reaction with 4 steps
1: 93 percent / NH2NH2, Et3N / ethanol / 2 h / Heating
2: 64 percent / I2, Et3N / dioxane / 0.5 h / Ambient temperature
3: 70 percent / N2 / ethanol
4: 81 percent / CrO3/pyridine / CH2Cl2 / 0.5 h / 22 °C

References:

Cox;Turner [Tetrahedron,1984,vol. 40,# 16,p. 3153 - 3158]

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