Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation

Alexander J. Grenning; Jonathan H. Boyce; John A. Porco

doi:10.1021/ja5060302

Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation

Alexander J. Grenning
, Jonathan H. Boyce
, John A. Porco

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

69 Scopus citations

Abstract

Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).

Original language	English (US)
Pages (from-to)	11799-11804
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	136
Issue number	33
DOIs	https://doi.org/10.1021/ja5060302
State	Published - Aug 20 2014
Externally published	Yes

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10.1021/ja5060302

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title = "Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation",

abstract = "Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).",

author = "Grenning, \{Alexander J.\} and Boyce, \{Jonathan H.\} and Porco, \{John A.\}",

year = "2014",

month = aug,

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doi = "10.1021/ja5060302",

language = "English (US)",

volume = "136",

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journal = "Journal of the American Chemical Society",

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T1 - Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation

AU - Grenning, Alexander J.

AU - Boyce, Jonathan H.

AU - Porco, John A.

PY - 2014/8/20

Y1 - 2014/8/20

N2 - Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).

AB - Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).

UR - https://www.scopus.com/pages/publications/84906337394

UR - https://www.scopus.com/pages/publications/84906337394#tab=citedBy

U2 - 10.1021/ja5060302

DO - 10.1021/ja5060302

M3 - Article

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AN - SCOPUS:84906337394

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation

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