Design and efficient synthesis of novel vitamin D analogues bearing an aniline moiety in their side chains

[Display omitted] •This convergent strategy could allow the obtaining of various derived analogues efficiently.•N-Alkylation allows the formation of analogues with secondary amines under mild conditions.•We have developed an efficient synthesis of six novel vitamin D3 analogues. Six novel vitamin D...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 61; no. 45; p. 152493
Main Authors:	Obelleiro, Antonio, Gómez-Bouzó, Uxía, Gómez, Generosa, Fall, Yagamare, Santalla, Hugo
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 05-11-2020
Subjects:	22-Substitued analogues Aza-analogues Calcitriol N-Alkylation Side-chain analogues N-Alkylation Side-chain analogues Aza-analogues 22-Substitued analogues Calcitriol
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Summary:	[Display omitted] •This convergent strategy could allow the obtaining of various derived analogues efficiently.•N-Alkylation allows the formation of analogues with secondary amines under mild conditions.•We have developed an efficient synthesis of six novel vitamin D3 analogues. Six novel vitamin D analogues bearing an aniline moiety in their side chains were designed and synthesized using a convergent route. The CD ring fragments were prepared from Inhoffen-Lythgoe diol in five- or six-steps with high yields. Secondary amines were obtained via a one-pot, two-step transformation with excellent yields.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2020.152493