Total syntheses of melodienones by redox isomerization of propargylic alcohols

2021 ◽  
Author(s):  
Chunmao Dong ◽  
Weiwei Peng ◽  
Huan Wang ◽  
Xiao Zhang ◽  
Jun Zhang ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Propargylic Alcohols ◽  
Rapid Construction ◽  
Redox Isomerization

A remarkable base-promoted methodology for rapid construction of the (E)- and (Z)-γ-oxo-α,β-alkenoic esters skeleton involved with readily accessed vinyl propargylic alcohols through modified redox isomerization was uncovered. This approach manifested...

Divergent Total Syntheses of Six Ganoderma Meroterpenoids: A Bioinspired Two-Phase Strategy

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1551-1554
Author(s):  
Yu-Ming Zhao ◽  
Fen Zhang
Keyword(s):  
Early Stage ◽  
Alder Reaction ◽  
Quinone Methide ◽  
Two Phase ◽  
Total Syntheses ◽  
Rapid Construction ◽  
Oxidative Aromatization ◽  
Key Steps ◽  
A Site ◽  
Site Selective

We briefly highlight our recent work on the total synthesis of six Ganoderma phenolic meroterpenoids: ganocins A–C, ganocochlearins A–D, and cochlearol T. Critical to this success was a bioinspired two-phase strategy that featured an early-stage rapid construction of a common planar tricyclic intermediate and late-stage highly selective transformations of this intermediate into various Ganoderma meroterpenoids. Key steps of the synthesis include a biomimetic ortho-quinone methide intramolecular hetero-Diels–Alder reaction, a Stahl-type oxidative aromatization, a nucleophilic dearomatization of a phenol, a regioselective 1,4-reduction of a dienone, a site-selective Mukaiyama hydration, and an intramolecular oxa-Michael addition/triflation cascade.

Remote C(sp3)–H vinylation via radical-mediated consecutive fission of C–H and C–C bonds

2020 ◽  
Vol 7 (19) ◽  
pp. 2981-2985
Author(s):  
Tao Niu ◽  
Shan Yang ◽  
Xinxin Wu ◽  
Chen Zhu
Keyword(s):  
Propargylic Alcohols

Described herein is a radical-mediated vinylation of the remote C(sp3)–H bonds of propargylic alcohols.

Gold Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Reaction Pathways to Access 1,3-Aminoalcohols, 3-Hydroxyketones or 3-Aminoketones

2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard
Keyword(s):  
Gold Catalysis ◽  
Reaction Pathways ◽  
High Yield ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
Catalytic Quantity ◽  
Selective Formation ◽  
General Method

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>

Development of Recent Total Syntheses Based on the Heck Reaction

2013 ◽  
Vol 17 (19) ◽  
pp. 2192-2224 ◽  
Author(s):  
Majid Heravi ◽  
Elaheh Hashemi ◽  
Nazanin Ghobadi
Keyword(s):  
Heck Reaction ◽  
Total Syntheses

Applications of Barton-McCombie Reaction in Total Syntheses

2014 ◽  
Vol 11 (6) ◽  
pp. 787-823 ◽  
Author(s):  
Majid Heravi ◽  
Atefe Bakhtiari ◽  
Zeinab Faghihi
Keyword(s):  
Total Syntheses
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