Biomimetic total synthesis of (±)-garcibracteatone

Henry P. Pepper; Hiu C. Lam; Witold M. Bloch; Jonathan H. George

doi:10.1021/ol302524q

Biomimetic total synthesis of (±)-garcibracteatone

Henry P. Pepper, Hiu C. Lam, Witold M. Bloch, Jonathan H. George

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

66 Citations (Scopus)

Abstract

The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.

Original language	English
Pages (from-to)	5162-5164
Number of pages	3
Journal	Organic Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1021/ol302524q
Publication status	Published - 5 Oct 2012
Externally published	Yes

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title = "Biomimetic total synthesis of (±)-garcibracteatone",

abstract = "The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.",

author = "Pepper, {Henry P.} and Lam, {Hiu C.} and Bloch, {Witold M.} and George, {Jonathan H.}",

year = "2012",

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AU - Pepper, Henry P.

AU - Lam, Hiu C.

AU - Bloch, Witold M.

AU - George, Jonathan H.

PY - 2012/10/5

Y1 - 2012/10/5

N2 - The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.

AB - The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.

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SP - 5162

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JO - Organic Letters

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IS - 19

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Biomimetic total synthesis of (±)-garcibracteatone

Abstract

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