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Stereoselective Total Synthesis of Goniothalesdiol A via Chiron Approach

✍ Scribed by Jhillu S. Yadav; Ragam Nageshwar Rao; Ragam Somaiah; Valaboju Harikrishna; Basi V. Subba Reddy

Book ID
102254641
Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
177 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using D‐ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy‐directed keto reduction, and intramolecular oxy‐Michael addition.

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Total Stereoselective Synthesis of (+)-G
Total Stereoselective Synthesis of (+)-Goniothalesdiol.
✍ M. Carmen Carreno; Gloria Hernandez-Torres; Antonio Urbano; Francoise Colobert 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 9 KB 👁 1 views

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First stereoselective total synthesis of
First stereoselective total synthesis of Goniothalesdiol A
✍ J.S. Yadav; N. Rami Reddy; V. Harikrishna; B.V. Subba Reddy 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 251 KB

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