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

Research output: Contribution to journal › Article › peer-review

41 Citations (SciVal)

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.

Original language	English
Pages (from-to)	4619-4621
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	24
DOIs	https://doi.org/10.1021/ol0357907
State	Published - Nov 27 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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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A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols

Abstract

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