Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System

Abstract An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. Graphic Abstract

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Novel Stereocontrolled Approach tosyn- andanti-Oxepene–Cyclogeranyltrans-Fused Polycyclic Systems: Asymmetric Total Synthesis of (−)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-Hydroxy-Palisadin B, and the AB Ring System of Adociasulfate-2 and Toxicol A

Chemistry - A European Journal ◽

10.1002/chem.200400407 ◽

2004 ◽

Vol 10 (15) ◽

pp. 3822-3835 ◽

Cited By ~ 33

Author(s):

Elias A. Couladouros ◽

Veroniki P. Vidali

Keyword(s):

Total Synthesis ◽

Ring System ◽

Asymmetric Total Synthesis ◽

Ab Ring

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Cover Picture: Novel Stereocontrolled Approach tosyn- andanti-Oxepene–Cyclogeranyltrans-Fused Polycyclic Systems: Asymmetric Total Synthesis of (−)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-Hydroxy-Palisadin B, and the AB Ring System of Adociasulfate-2 and Toxicol A (Chem. Eur. J. 15/2004)

Chemistry - A European Journal ◽

10.1002/chem.200490051 ◽

2004 ◽

Vol 10 (15) ◽

pp. 3595-3595

Author(s):

Elias A. Couladouros ◽

Veroniki P. Vidali

Keyword(s):

Total Synthesis ◽

Ring System ◽

Asymmetric Total Synthesis ◽

Ab Ring

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ChemInform Abstract: Asymmetric Total Synthesis of Propindilactone G. Part 2. Enantioselective Construction of the Fully Functionalized BCDE Ring System.

ChemInform ◽

10.1002/chin.201628233 ◽

2016 ◽

Vol 47 (28) ◽

Author(s):

Jia-Jun Zhang ◽

Lin You ◽

Yue-Fan Wang ◽

Yuan-He Li ◽

Xin-Ting Liang ◽

...

Keyword(s):

Total Synthesis ◽

Ring System ◽

Asymmetric Total Synthesis

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Asymmetric Total Synthesis of Crotophorbolone: Construction of the 5/7/6-Fused Ring System via an α-Alkoxy Bridgehead Radical Reaction

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.20160208 ◽

2016 ◽

Vol 89 (10) ◽

pp. 1137-1144 ◽

Cited By ~ 7

Author(s):

Daisuke Urabe ◽

Taro Asaba ◽

Masayuki Inoue

Keyword(s):

Total Synthesis ◽

Radical Reaction ◽

Ring System ◽

Asymmetric Total Synthesis ◽

Fused Ring ◽

Fused Ring System

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Concise Total Synthesis of Curvulone B

Synlett ◽

10.1055/a-1297-6838 ◽

2020 ◽

Author(s):

Debendra K. Mohapatra ◽

Shivalal Banoth ◽

Utkal Mani Choudhury ◽

Kanakaraju Marumudi ◽

Ajit C. Kunwar

Keyword(s):

Total Synthesis ◽

Stereoselective Synthesis ◽

Ring System ◽

Bond Forming ◽

Cross Metathesis ◽

Bond Forming Reactions ◽

Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

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