Studies on a Total Synthesis of Plakotenin: Synthesis of Optically Active trans-Hydrindanes by Diastereoselective Asymmetric Intramolecular Diels-Alder Reaction

Ishizaki, Miyuki; Hara, Yoshiyori; Kojima, Satoshi; Hoshino, Osamu

doi:10.3987/com-98-s(h)72

Cited by 14 publications

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Stereocontrolled Total Synthesis of theStemona Alkaloid (−)-Stenine

et al. 2001

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The Stemona alkaloid stenine (1), isolated from Stemona tuberosa of physiologically active stemonaceous plants, possesses the structurally novel and unique azepinoindole skeleton (B,C,D-ring system). We have achieved the asymmetric total synthesis of (-)-stenine (1), starting from 1,5-pentanediol (10). The key features are an intramolecular diastereoselective Diels-Alder reaction of the (E,E,E) triene 6, prepared in a convergent fashion from three components--dienyl chloride 7, dithiane 8, and chiral phosphonate 9--and efficient construction of the tricyclic A,B,D-ring system 29 through thermodynamically controlled regioselective enolization of the bicyclic ketone 25. In this article, we describe in detail the highly stereocontrolled total synthesis of (-)-stenine (1). These results should be useful for the asymmetric total synthesis of another, more complex. molecule: tuberostemonine (2), the synthesis of which has never been reported.

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Stereocontrolled Total Synthesis of theStemona Alkaloid (−)-Stenine

et al. 2001

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Porifera (Sponges)–5

Kornprobst

2014

Encyclopedia of Marine Natural Products

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Enantioselective Total Synthesis of (−)‐Hosieine A

Ouyang

Yan

et al. 2015

Angewandte Chemie

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The first total synthesis of (À)-hosieine Aw as accomplished and features an unprecedented nitroso-ene cyclization to construct the 2-azabicyclo[3.2.1]octane ring system. Phosphine-enabled stereoselective bromohydrination provided interesting mechanistic insights into the anti-Markovnikov process.A lso noteworthy is the retention of stereochemistry at C9 in the facile radical debromination initiated by Et 3 B/air.

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Studies on a Total Synthesis of Plakotenin: Synthesis of Optically Active trans-Hydrindanes by Diastereoselective Asymmetric Intramolecular Diels-Alder Reaction

Cited by 14 publications

References 0 publications

Stereocontrolled Total Synthesis of theStemona Alkaloid (−)-Stenine

Stereocontrolled Total Synthesis of theStemona Alkaloid (−)-Stenine

Porifera (Sponges)–5

Enantioselective Total Synthesis of (−)‐Hosieine A

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