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Asymmetric total synthesis of $(+)$-$\Delta ^{9(12)}$-capnellene


Meyers, A I; Bienz, Stefan (1990). Asymmetric total synthesis of $(+)$-$\Delta ^{9(12)}$-capnellene. Journal of Organic Chemistry, 55(3):791-798.

Abstract

The first asymmetric total synthesis of the unnatural enantiomer of (-)-A9(12)-capnellene has been achieved in 14.1 % overall yield. The synthesis is based on the chiral nonracemic bicyclic lactam 15 derived from inexpensive (S)-valinol and levulinic acid. The goal of the synthesis, which was accomplished, was to reach the intermediate 13, originally reported in racemic form, and carry out the last step to the title compound.

Abstract

The first asymmetric total synthesis of the unnatural enantiomer of (-)-A9(12)-capnellene has been achieved in 14.1 % overall yield. The synthesis is based on the chiral nonracemic bicyclic lactam 15 derived from inexpensive (S)-valinol and levulinic acid. The goal of the synthesis, which was accomplished, was to reach the intermediate 13, originally reported in racemic form, and carry out the last step to the title compound.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1990
Deposited On:24 Aug 2017 15:12
Last Modified:21 Feb 2018 09:08
Publisher:American Chemical Society (ACS)
ISSN:0022-3263
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/jo00290a005

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