Ramana, C .V. ; Pandey, Sunil Kumar (2010) A modular total synthesis of aculeatins A, B, E, F and 6-epi-aculeatins E, F Tetrahedron, 66 (1). pp. 390-399. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tet.2009.10.058
Abstract
The total synthesis of aculeatins A, B, E and F confirming the assigned absolute configuration of recently isolated aculeatins E and F is documented. A convergent approach has been designed by the addition of both the terminal units (phenol and side chain) at an advanced stage. The central 1,3,5-triol unit with the requisite stereochemistry was prepared from the commercially available α-d-glucoheptonic-γ-lactone. Selective O-debenzylation during the hydrogenolysis of the diyne intermediate and the one pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total syntheses.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Natural Products Synthesis; Aculeatins; Alkyne–Oxirane Coupling; Oxidative Spiroketalization; Sonogashira Coupling |
| ID Code: | 106065 |
| Deposited On: | 01 Feb 2018 16:54 |
| Last Modified: | 01 Feb 2018 16:54 |
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