Total synthesis of (-)-heliespirone a and (+)-heliespirone C
Total syntheses of the spiro-epimeric natural products (-)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa-Michael addition.
Synthesis of Highly Enantio-Enriched Heliespirones A and C by a Diastereoselective Aromatic Claisen Rearrangement
Computational methods were used to investigate the stereochemical course of the extra-annular Claisen rearrangement. The stereochemical fidelity of the synthetic strategy and comparison of the optical properties support the hypothesis that the heliespirones are scalemic natural products.
Norcott, Philip,McErlean, Christopher S. P.
p. 366 - 372
(2018/05/31)
Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement
The total synthesis of heliannuol C and E from a common intermediate are described. Key steps in the synthesis include a regioselective aromatic Claisen rearrangement to install the (1-vinyl)-4-methyl-3-pentenyl substituent and regioselective biomimetic 7
Vyvyan, James R.,Oaksmith, Jennifer M.,Parks, Bevin W.,Peterson, Elaine M.
p. 2457 - 2460
(2007/10/03)
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