Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide | Zendy

Étienne Fleury | Zendy; MarieIsabelle Lannou | Zendy; Olivia Bistri | Zendy; François Sautel | Zendy; Georges Massiot | Zendy; Ange Pancrazi | Zendy; Janick Ardisson | Zendy

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Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

Author(s) -

Étienne Fleury,

MarieIsabelle Lannou,

Olivia Bistri,

François Sautel,

Georges Massiot,

Ange Pancrazi,

Janick Ardisson

Publication year - 2009

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo9012833

Subject(s) - polyketide , chemistry , diastereomer , aldol reaction , stereochemistry , fragment (logic) , natural product , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , biosynthesis , computer science , programming language , enzyme

The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

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