Collective total synthesis of PPAPs: Total synthesis of clusianone via intramolecular cyclopropanation

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8 Citations (Scopus)

Abstract

The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.

Original languageEnglish
Pages (from-to)955-959
Number of pages5
JournalNatural Product Communications
Volume8
Issue number7
Publication statusPublished - 2013

Fingerprint

synthesis
Hydrogenation
hyperforin
hydrogenation
chemical derivatives
7-epiclusianone
N-(3-phenyl-n-propyl)-1-phenyl-2-aminopropane
garsubellin A
bicyclo(3.3.1)nonane
prenyl
nemorosone
cyclopropane

Keywords

  • Clusianone
  • Cyclopropanation
  • Natural product
  • Stereoselectivity
  • Total synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Complementary and alternative medicine
  • Plant Science

Cite this

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abstract = "The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.",
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AU - Uwamori, Masahiro

AU - Nakada, Masahisa

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N2 - The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.

AB - The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.

KW - Clusianone

KW - Cyclopropanation

KW - Natural product

KW - Stereoselectivity

KW - Total synthesis

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