Asymmetric Total Synthesis of Cephanolide A.,Angewandte Chemie International Edition

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Asymmetric Total Synthesis of Cephanolide A.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-08-04 , DOI: 10.1002/anie.202009562
Hongyuan Zhang ₁ , Haibing He ₂ , Shuanhu Gao _{1,

2}

Affiliation

The first asymmetric total synthesis of cephanolide A, a complex hexacyclic C₁₈ dinorditerpenoid from cephalotaxus sinensis, was achieved. The synthesis features a convergent strategy, which provides a flexible approach to prepare the biogenetically cephalotaxus diterpenoids and structurally related derivatives for biological studies. A mild intramolecular Prins cyclization was developed to construct the central hexahydrofluorenol skeleton (A‐B‐C ring), which relies on the originally proposed hydroacylation strategy. A remote hydroxy group directed hydrogenation was applied to stereospecifically reduce the tetra‐substituted enone unit. A sequence of ring forming steps, including lactonization, cation mediated etherification and Friedel–Crafts cyclization, was efficiently utilized to forge the cage‐like skeleton.

更新日期：2020-08-04

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