Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels–Alder reaction: Total synthesis of (−)-himbacine

2018 ◽  
Vol 26 (7) ◽  
pp. 1378-1386 ◽  
Author(s):  
Koji Sugiyama ◽  
Shinji Kawanishi ◽  
Yasuhiro Oki ◽  
Marin Kamiya ◽  
Ryosuke Hanada ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Kinetic Resolution ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dynamic Kinetic Resolution ◽  
One Pot ◽  
Diels Alder Reaction

Four-step one-pot catalytic asymmetric synthesis of multisubstituted tricyclic compounds: Lipase-catalyzed dynamic kinetic resolution followed by an intramolecular Diels–Alder reaction

Synlett ◽  
2021 ◽  
Author(s):  
Izuru Tsuchimochi ◽  
Shuhei Hori ◽  
Yasuo Takeuchi ◽  
Masahiro Egi ◽  
Tomo-o Satoh ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Kinetic Resolution ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Tricyclic Compounds ◽  
High Yields ◽  
Group Migration ◽  
Oxovanadium Compounds

Starting from readily available tertiary alcohols, four different reactions (i.e., a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels–Alder reaction) took place under the co-catalysis of lipase and oxovanadium compounds in a one-pot process to produce multisubstituted tricyclic carbon frameworks in high yields and high enantioselectivities. The key to the success of this process was the discovery that the silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.

scholarly journals A Versatile, Diels–Alder Reaction-Based Approach to Prenyleudesmane Diterpenoids: A Concise Total Synthesis of Sinupol

Synlett ◽  
2020 ◽  
Vol 31 (10) ◽  
pp. 1007-1010
Author(s):  
Koichiro Ota ◽  
Hiroaki Miyaoka ◽  
Kazuo Kamaike
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Biologically Active ◽  
Diels Alder Reaction ◽  
Step Procedure

Herein, a concise strategy designed to provide general and diversifiable access to various prenyleudesmane terpenoids is described and utilized in the asymmetric synthesis of a biologically active prenyleudesmane diterpenoid, sinupol, which is accomplished in a seven-step procedure.

One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties

2016 ◽  
Vol 14 (8) ◽  
pp. 2444-2453 ◽  
Author(s):  
Ji-Yao Li ◽  
Zhi-Long Li ◽  
Wei-Wei Zhao ◽  
Yan-Kai Liu ◽  
Zhi-Ping Tong ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Highly Efficient ◽  
Diels Alder Reaction

Lactols or cyclic hemiaminals are directly used as nucleophiles in the asymmetric aza-Diels–Alder reaction to synthesize ring-fused piperidine derivatives.

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