Synthesis of neplanocin A and its 3'-epimer via an intramolecular Baylis-Hillman reaction.

Tan, Yun Xuan; Santhanakrishnan, Sridhar; Yang, Hai Yan; Chai, Christina L L; Tam, Eric Kwok Wai

Tan, Yun Xuan; Santhanakrishnan, Sridhar; Yang, Hai Yan; Chai, Christina L L; Tam, Eric Kwok Wai.

Afiliación

Tan YX; Institute of Chemical & Engineering Sciences, A*STAR (Agency for Science, Technology and Research) , 8 Biomedical Grove, Neuros#07-01, Singapore 13866.

J Org Chem ; 79(17): 8059-66, 2014 Sep 05.

Article en En | MEDLINE | ID: mdl-25122518

ABSTRACT

ABSTRACT

The key cyclopentenyl intermediate 11b was synthesized in 4 steps from d-ribose in 41% overall yield via an efficient intramolecular Baylis-Hillman reaction. This novel key intermediate can be modified easily and transformed to neplanocin A (1a) and its 3'-epimer (1b).

Asunto(s)

Adenosina/análogos & derivados; Ciclopentanos/química; Adenosina/síntesis química; Adenosina/química; Catálisis; Técnicas Químicas Combinatorias; Estructura Molecular; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Adenosina / Ciclopentanos Idioma: En Revista: J Org Chem Año: 2014 Tipo del documento: Article

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