4.4 Article

A concise total synthesis of (+)-pyrenolide D

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 25, Pages 3278-3280

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.04.044

Keywords

Pyrenolide D; Hemiketal; Xylose; Natural product; Spiroketalization

Funding

  1. MOST of China [2012CB822101, 2012ZX09502001-001]
  2. NNSF of China [21072217, 21202193]

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The concise total synthesis of antitumor natural product (+)-pyrenolide D has been achieved in seven steps from readily available natural carbohydrate D-xylose with 10.8% overall yield. The key steps involved methylpropiolate-mediated stereoselective alkynylation on lactone carbonyl group and the tandem one-pot desilylation-spirolactonization. (C) 2013 Elsevier Ltd. All rights reserved.

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