Stereodivergent Synthesis and Relative Stereostructure of the C1–C13 Fragment of Symbiodinolide

Four possible diastereomers of the C1–C13 fragment of symbiodinolide, which were proposed by the stereostructural analysis of the degraded product, were synthesized in a stereodivergent and stereoselective manner. The key transformations were aldol reaction of methyl acetoacetate with the aldehyde,...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-03, Vol.80 (6), p.3111-3123
Main Authors: Takamura, Hiroyoshi, Wada, Hiroko, Ogino, Mao, Kikuchi, Takahiro, Kadota, Isao, Uemura, Daisuke
Format: Article
Language:English
Subjects:
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Molecular Structure
Stereoisomerism
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Summary:Four possible diastereomers of the C1–C13 fragment of symbiodinolide, which were proposed by the stereostructural analysis of the degraded product, were synthesized in a stereodivergent and stereoselective manner. The key transformations were aldol reaction of methyl acetoacetate with the aldehyde, diastereoselective reduction of the resulting β-hydroxy ketone, and the stereoinversion at the C6 position. Comparison of the 1H NMR data between the four synthetic products and the degraded product revealed the relative stereostructure of the C1–C13 fragment of symbiodinolide.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00027