Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

Itagaki, Noriaki; Iwabuchi, Yoshiharu

doi:10.1039/b616641e

Cited by 29 publications

(15 citation statements)

References 19 publications

(7 reference statements)

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“…Oxidation with PCC followed by double bond hydrogenation using Pd/C gave (±)-boschnialactone 454 in 75% yield ( Scheme 81 ). Additional applications of this photoinduced α-cleavage/hydrogen abstraction sequence can be found in the synthesis of (+)-juvabione ( 459 , Scheme 82 ) 353 and (±)-hop ether. 354 …”

Section: Norrish-type Photoreactionsmentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

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Section: Norrish-type Photoreactionsmentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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“…After a Norrish-I-type fragmentation to give aldehyde 25, eight further steps were required to finish an enantioselective synthesis of (+)-juvabione. [25] …”

Section: Intramolecular Aldolizationmentioning

confidence: 97%

Organocatalytic Synthesis of Drugs and Bioactive Natural Products

2007

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“…In contrast, organocatalyst cis ‐silyloxy‐ d ‐proline 49 gave rise to enantiomer (+)‐ 51 in good yields and excellent diastereo‐ and enantioselectivity. The same research group described the transformation of (+)‐ 51 into key intermediate (+)‐ 52 , which gave, after two different Michael additions, natural sesquiterpene (+)‐juvabione and potent cannabinoid receptor agonist (−)‐CP‐55 940 …”

Section: Organocatalysts Derived From Post‐translational Amino Acidsmentioning

confidence: 99%

Organocatalysts Derived from Unnatural α‐Amino Acids: Scope and Applications

Agirre

Arrieta

Arrastia

et al. 2018

Chemistry An Asian Journal

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The organocatalytic properties of unnatural aamino acids are reviewed. Post-translational derivatives of natural a-aminoa cids include 4-hydroxy-l-proline and 4amino-l-proline scaffolds, and also prolineh omologues. The activity of synthetic unnatural a-amino acid-based organocatalysts, such as b-alkyl alanines, alanine-based phosphines, and tert-leucine derivatives, are reviewed herein. The orga-nocatalytic properties of unnatural monocyclic,b icyclic, and tricyclicproline derivatives are also reviewed. Severalfamilies of these organocatalystsp ermitthe efficient and stereoselective synthesis of complex natural products. Most of the reviewedo rganocatalysts accelerate the reported reactions through covalent interactions that raise the HOMO (enamine intermediates) or lower the LUMO (iminiumintermediates).Scheme1.Ageneral (simplified) mechanism of addition reactionsbye namine organocatalysis promoted by a-amino acid derivatives.[a] M.

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Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

Abstract: (+)-Juvabione, a natural sesquiterpene exhibiting insect juvenile hormone activity, has been synthesized from sigma-symmetric 4-(2-formyl-ethyl)cyclohexanone by employing organocatalytic asymmetric aldolization and Norrish I-type fragmentation as the key steps.

Cited by 29 publications

References 19 publications

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Organocatalytic Synthesis of Drugs and Bioactive Natural Products

Organocatalysts Derived from Unnatural α‐Amino Acids: Scope and Applications

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