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First stereoselective total synthesis of Goniothalesdiol A

✍ Scribed by J.S. Yadav; N. Rami Reddy; V. Harikrishna; B.V. Subba Reddy

Book ID: 104096192
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 251 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.01.050

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✦ Synopsis

The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition.

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