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Synthesis 2015; 47(19): 2997-3008
DOI: 10.1055/s-0034-1380864
DOI: 10.1055/s-0034-1380864
paper
Stereoselective Total Synthesis of (+)-Anamarine and 8-epi-(–)-Anamarine from d-Mannitol
Further Information
Publication History
Received: 12 February 2015
Accepted after revision: 24 April 2015
Publication Date:
30 June 2015 (online)
Abstract
Stereoselective total synthesis of (+)-anamarine and the first synthesis of 8-epi-(–)-anamarine, its nonnatural diastereomer, were achieved from readily available d-mannitol. The key reactions involved were asymmetric dihydroxylation, cross-metathesis and ring-closing metathesis reactions. The approach is adoptable advantageously for the diversity-oriented synthesis of several related classes of natural products.
Key words
(+)-anamarine - 8-epi-(–)-anamarine - d-mannitol - asymmetric dihydroxylation - cross-metathesis and ring-closing metathesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380864.
- Supporting Information
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