Enantioselective Total Synthesis of (+)-Tricycloclavulone

Enantioselective Total Synthesis of (+)-Tricycloclavulone

The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,0 , ]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting...

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Veröffentlicht in:Journal of the American Chemical Society 2004-04, Vol.126 (14), p.4520-4521
Hauptverfasser: Ito, Hisanaka, Hasegawa, Mineki, Takenaka, Yosuke, Kobayashi, Tatsuya, Iguchi, Kazuo
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Sprache:eng
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Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Prostaglandins - chemical synthesis
Stereoisomerism
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container_end_page 4521
container_issue 14
container_start_page 4520
container_title Journal of the American Chemical Society
container_volume 126
creator Ito, Hisanaka
Hasegawa, Mineki
Takenaka, Yosuke
Kobayashi, Tatsuya
Iguchi, Kazuo
description The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,0 , ]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting an intramolecular ester transfer reaction, and asymmetric reduction of the carbonyl group on the α-chain using Noyori's chiral ruthenium catalyst.
doi_str_mv 10.1021/ja049750p
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subjects Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Prostaglandins - chemical synthesis
Stereoisomerism
title Enantioselective Total Synthesis of (+)-Tricycloclavulone
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