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Synthesis 2016; 48(23): 4300-4304
DOI: 10.1055/s-0035-1561491
DOI: 10.1055/s-0035-1561491
paper
Protecting-Group-Free Total Synthesis of 8-Methoxygoniodiol
Further Information
Publication History
Received: 07 May 2016
Accepted after revision: 09 June 2016
Publication Date:
21 July 2016 (online)
Abstract
A concise stereoselective total synthesis of the naturally occurring styryl lactone 8-methoxygoniodiol in five simple steps from readily available inexpensive trans-cinnamaldehyde is described. The efficient synthesis features a successful protecting-group-free strategy, with desirable step- and atom-economy. The synthetic strategy relies on a Maruoka asymmetric allylation, an epoxidation, a ring-closing metathesis, and a stereoselective epoxide ring opening as key steps.
Key words
lactones - methoxygoniodiol - natural products - total synthesis - Maruoka allylation - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561491.
- Supporting Information
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