A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols

Roxana Ciochina; Robert B. Grossman

doi:10.1021/ol0357907

A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols

Roxana Ciochina
, Robert B. Grossman

Chemistry

Producción científica: Article › revisión exhaustiva

42 Citas (Scopus)

Resumen

(Equation presented) The three-carbon α,α′-annulation of a sterically hindered cyclic β-keto ester can be achieved by alkynylation with 3,3-dietnoxypropyne, syn reduction of the alkyne with Co ₂(CO)₈ and Et₃SiH, and an intramolecular aldol reaction. The method is potentially useful for the synthesis of nemorosone, hyperforin, and other polycyclic polyprenylated acylphloroglucinols.

Idioma original	English
Páginas (desde-hasta)	4619-4621
Número de páginas	3
Publicación	Organic Letters
Volumen	5
N.º	24
DOI	https://doi.org/10.1021/ol0357907
Estado	Published - nov 27 2003

Financiación

Financiadores	Número del financiador
National Institute of General Medical Sciences	R01GM061002

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0357907

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title = "A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols",

abstract = "(Equation presented) The three-carbon α,α′-annulation of a sterically hindered cyclic β-keto ester can be achieved by alkynylation with 3,3-dietnoxypropyne, syn reduction of the alkyne with Co 2(CO)8 and Et3SiH, and an intramolecular aldol reaction. The method is potentially useful for the synthesis of nemorosone, hyperforin, and other polycyclic polyprenylated acylphloroglucinols.",

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N2 - (Equation presented) The three-carbon α,α′-annulation of a sterically hindered cyclic β-keto ester can be achieved by alkynylation with 3,3-dietnoxypropyne, syn reduction of the alkyne with Co 2(CO)8 and Et3SiH, and an intramolecular aldol reaction. The method is potentially useful for the synthesis of nemorosone, hyperforin, and other polycyclic polyprenylated acylphloroglucinols.

AB - (Equation presented) The three-carbon α,α′-annulation of a sterically hindered cyclic β-keto ester can be achieved by alkynylation with 3,3-dietnoxypropyne, syn reduction of the alkyne with Co 2(CO)8 and Et3SiH, and an intramolecular aldol reaction. The method is potentially useful for the synthesis of nemorosone, hyperforin, and other polycyclic polyprenylated acylphloroglucinols.

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JO - Organic Letters

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A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols

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