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Total Synthesis of (+)-Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels—Alder Dimerization of Orthoquinols with a C2-Symmetric Transition State.

✍ Scribed by Julien Gagnepain; Frederic Castet; Stephane Quideau

Publisher
John Wiley and Sons
Year
2007
Weight
15 KB
Volume
38
Category
Article
ISSN
0931-7597

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Total Synthesis of (+)-Aquaticol by Biom
Total Synthesis of (+)-Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a C2-Symmetric Transition State
✍ Julien Gagnepain; Frédéric Castet; Stéphane Quideau 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 208 KB

The absolute configuration of (þ)-aquaticol (1 a) described in this Communication should be revised to 3S,10S,14R,23R as shown on the structure below and its accompanying ORTEP diagram (monoclinic, P2 1 , Flack factor = À0.2(2), CCDC-295794). (þ)-Aquaticol was derived from SIBX-mediated oxidation of