Total synthesis of a C15 ginkgolide, (.+-.)-bilobalide

Corey, E. J.; Su, Wei

doi:10.1021/ja00258a050

Cited by 99 publications

(48 citation statements)

References 1 publication

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“…[46] Next, the dimethyl acetals were converted into the synthetically valuable methyl esters using mCPBA/ BF 3 · OEt 2 ( Table 5). [47] For the specific case of our Heck products 3, this was a challenging transformation due to the liability of β-aryloxy esters under Lewis acid conditions. Oxidation of compound 3 e with mCPBA led to the corresponding ester 7 a in a modest 25% yield.…”

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

et al. 2019

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Herein we report the enantioselective Heck‐Matsuda arylation of acyclic E and Z‐alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck‐Matsuda arylation has shown a broad scope (25 examples), and some key Heck‐Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)‐Fluoxetine, (R)‐Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory.

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Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

et al. 2019

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“…[77] Analysis of the tetracyclic structure led Corey and Su to alkyne 107 and (+)- trans -1,2-cyclohexene dicarboxylic acid dimenthoxy ester (chiron 108 ) as starting materials which would end up in a bicylic intermediate bearing all the requisite carbon atoms of the target compound (Scheme 11). It is of interest that chiron 108 shows no visually evident overlap with any of the rings in bilobalide.…”

Section: Bilobalidementioning

confidence: 99%

“…This reaction can also be performed using 108 and 2 equivalents of LDA as was done in the original synthesis of racemic bilobalide. [77,80] Ketone 112 was reduced to the corresponding allylic alcohol (>10:1) by CBS reduction.…”

Section: Bilobalidementioning

confidence: 99%

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

et al. 2016

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Strategies for the total synthesis of complex natural products that contain two or more contiguous stereogenic quarternary carbon atoms in their intricate structures are reviewed with twelve representative examples. Emphasis has been put on the methods to create quarternary carbon stereocenters, including syntheses of the same natural product from different groups, thereby showcasing diversity of thought and individual creativity. A compendium of selected natural products containing two or more contiguous stereogenic quarternary carbon atoms and key reactions in their total or partial syntheses is provided in the Supporting Information section.

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“…tiopure bilobalide (1) was developed by Corey et al in 1987Corey et al in / 1988. [9,10] Crimmins et al published a shorter total synthesis of racemic bilobalide (1) in 1993. [11] Photochemical reactions provide access to complex structures, which cannot easily be obtained by classical methods.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Approaches to the Bilobalide Core

Emsermann

Opatz

2017

Eur J Org Chem

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Bilobalide is a tetracyclic sesquiterpene containing three contiguous γ‐lactone rings and an unusual tert‐butyl group, which is found in the leaves of the ginkgo tree (Ginkgo biloba). Three different photochemical approaches towards bilobalide's unique skeleton are presented. A meta photocycloaddition, a [2 + 2] photocycloaddition, and a Paternò–Büchi‐reaction were chosen as the respective key steps.

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Total synthesis of a C15 ginkgolide, (.+-.)-bilobalide

Cited by 99 publications

References 1 publication

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

Photochemical Approaches to the Bilobalide Core

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