Concise synthesis and characterization of novel seco-steroids bearing a spiro-oxetane instead of a metabolically labile C3-hydroxy group

Autor:	Tsutomu Suenaga, Toshie Fujishima, Takato Nozaki
Rok vydání:	2014
Předmět:	Receptor complex Circular dichroism Stereochemistry Chemistry medicine.medical_treatment Organic Chemistry Hydroxy group Absolute configuration Oxetane Biochemistry Benzoates Steroid chemistry.chemical_compound Drug Discovery medicine Chirality (chemistry)
Zdroj:	Tetrahedron Letters. 55:3805-3808
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.05.060
Popis:	Two novel stereoisomeric analogues of 1,25-dihydroxyvitamin D3 bearing a spiro-oxetane at the C3 position of the A-ring have been designed and synthesized in a convergent manner. The absolute configuration at the C1 position of the synthesized compounds was determined by the circular dichroism exciton chirality method using the corresponding C1-allylic benzoates. The replacement of the C3-hydroxy group with a spiro-oxetane provided an advantageous conformational preference for the parent seco-steroids, which would facilitate the formation of a stable receptor complex.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eb96daf0f9f85c91dd77423d8873a708 https://doi.org/10.1016/j.tetlet.2014.05.060 Zobrazit plný text záznamu Full Text from ScienceDirect