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Synthetic studies on C14 cembranoids: synthesis of C4–12 fragment of sarcophytonolides E–G and L and C5–11 fragment of sarcophytonolide L

✍ Scribed by Rodney A. Fernandes; Arun B. Ingle

Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 390 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.11.093

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✦ Synopsis

An efficient stereoselective synthesis of C4-12 fragment of the cembranoids, sarcophytonolides E-G and L and C5-11 fragment of sarcophytonolide L is described. The C4-12 building block is efficiently assembled starting from chiral pool material (R)-carvone employing the Baeyer-Villiger oxidation, modified Knoevenagel condensation and asymmetric dihydroxylation as the key steps. The synthesis of C5-11 fragment is based on orthoester Johnson-Claisen rearrangement as the key step.

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