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Synthesis 2014; 46(03): 307-312
DOI: 10.1055/s-0033-1340314
DOI: 10.1055/s-0033-1340314
paper
First Total Synthesis of Lippialactone and Its C9 Epimer
Authors
Further Information
Publication History
Received: 25 September 2013
Accepted after revision: 07 November 2013
Publication Date:
06 December 2013 (online)
Abstract
This paper describes the first total synthesis of bioactive lippialactone and C9-epi-lippialactone adopting Keck asymmetric allylation/Barbier allylation and olefin cross-metathesis as the key steps.
Key words
lippialactone - 6-substituted α,β-unsaturated δ-lactones - l-threonine - Keck allylation - Barbier allylation - cross-metathesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information (PDF)
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- 15 The diastereomeric ratio of 7a/7b was determined by 1H NMR analysis of the mixture, from the relative integration of the well-resolved, diagnostic protons due to O-CH2-O (MOM) which resonated in 7a at δ 4.80 (q, J = 6.8 Hz), 4.72 (d, J = 6.8 Hz) and 4.64 (d, J = 6.8 Hz), while in 7b the same protons were observed at δ 4.76 (d, J = 6.8 Hz) and 4.70 (q, J = 7.0 Hz). Further, the O-CH3 (MOM) protons appeared at δ 3.46 and 3.39 as singlets in 7a, while in 7b the same protons were observed at δ 3.43 and 3.41. The ratio was also confirmed by HPLC analysis {LCMS [column: XDB-C18, 30% H2O (NH4OAc, 10 mmol) in MeCN, flow rate: 1 mL/min, 230 nm]: t R (major) = 3.825 min, t R (minor) = 4.158 min}.