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Stereoselective synthesis of iriomoteolide-1a hemiketal core

✍ Scribed by Jun Xie; David A. Horne

Book ID: 104096642
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 455 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.05.092

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✦ Synopsis

A stereoselective synthesis of the cyclic hemiketal core of iriometeolide-1a (1) is described. The key step involves a Sakurai reaction of allylsilane 4 and aldehyde 5, which bears a chiral a-tertiary center. Mild TES deprotection of b,c-unsaturated ketone 23 led to concomitant cyclization to produce the fully intact hemiketal core 2.

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