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

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.

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ChemInform Abstract: Chiral Amino Siloxy Dienes in the Diels-Alder Reaction: Applications to the Asymmetric Synthesis of 4-Substituted and 4,5-Disubstituted Cyclohexenones and the Total Synthesis of (-)-α-Elemene.

ChemInform ◽

10.1002/chin.200005030 ◽

2010 ◽

Vol 31 (5) ◽

pp. no-no

Author(s):

Sergey A. Kozmin ◽

Viresh H. Rawal

Keyword(s):

Total Synthesis ◽

Asymmetric Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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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

Bioorganic & Medicinal Chemistry ◽

10.1016/j.bmc.2017.08.019 ◽

2018 ◽

Vol 26 (7) ◽

pp. 1378-1386 ◽

Cited By ~ 5

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

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Chiral Amino Siloxy Dienes in the Diels−Alder Reaction: Applications to the Asymmetric Synthesis of 4-Substituted and 4,5-Disubstituted Cyclohexenones and the Total Synthesis of (−)-α-Elemene

Journal of the American Chemical Society ◽

10.1021/ja9921930 ◽

1999 ◽

Vol 121 (41) ◽

pp. 9562-9573 ◽

Cited By ~ 42

Author(s):

Sergey A. Kozmin ◽

Viresh H. Rawal

Keyword(s):

Total Synthesis ◽

Asymmetric Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽

10.1055/a-1517-7515 ◽

2021 ◽

Author(s):

Fabian Hofmann ◽

Cornelius Gärtner ◽

Martin Kretzschmar ◽

Christoph Schneider

Keyword(s):

Asymmetric Synthesis ◽

Alder Reaction ◽

Single Step ◽

Diels Alder ◽

Quinone Methide ◽

Bronsted Acid ◽

Atom Economy ◽

Diels Alder Reaction ◽

Brönsted Acid ◽

Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

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